Lose My Mind
by AwfullyGastly
Summary: A crossover AU where Caroline is dating Sam Winchester. She sets Elena up for a blind-date with her boyfriend's brother, Dean. After the date goes badly, Elena thinks she wouldn't ever see him again, that is until she finds out Caroline is engaged. Dean/Elena Sam/Caroline
1. First

"Caroline you've got to be kidding me! This is the 3rd date you've tried to get me to go on." She whines into the speaker of her phone.

"Elena, come on! Please! Please, please, please," Elena rolls her eyes as Caroline begs on the other line. "I promise you'll like him."

"Care, you said that about the last two guys!" Elena lets herself drop onto her mattress as the memories of her previous 2 blind dates enter her mind. She swore off dating after she caught the last one slipping a little _something_ in her drink when she had gone to the restroom.

"Okay, I admit... my radar was a little off the last 2 times. But I promise, Elena. This guy is perfect for you."

"Care..."

"If it's any comfort, he's Sam's older brother. And let me just say, looks like the genes in Winchester pool are generous."

Elena laughs at Caroline's comment; remembering the day she and Caroline had met Sam at Whitmore.

 _It had been about a year ago. Caroline had managed to trick Elena into helping her move into her new dorm. The two girls were carrying boxes up the stairs, when suddenly someone crashes into Caroline, causing her box to fall, break open and spill out all its contents down the stairs._

 _"Oh. My. God," She emphasized each word. "You cannot be serious," Caroline's temper was on the verge of rising, until she saw the eyes of the man she had crashed into. The rage she was beginning to feel slowly diminished; almost as if the pair of hazel eyes she was looking into were cooling her down._

 _"I'm so sorry. I didn't see you, I was reading," He lifted up a pamphlet he held in his hand._

 _Caroline quickly shook him off. "Oh, don't worry about it. It's okay," She smiled at him. He returned her smile with his own dimpled one._

 _Elena watched from the stairs as the two introduced one another; a small smile growing on her lips as she slowly began to realize, they'd just made a new friend._

"Elena!" Caroline's voice brought Elena back from her thoughts. "Are you even listening to me?"

"Yes, Care," She lied. "But I really don't want to go another date..."

"Please," Caroline began to plead again, causing Elena to roll her eyes. "I promise you'll love him, Elena. He's really great!"

She bit her lip as she considered Caroline's request. After a moment of a small inner pros and cons debate, she finally agreed. "Fine, I'll go." She replied. Elena quickly moved the phone from her ear as soon as she heard Caroline begin to squeal in excitement on the other end.

After a moment of Caroline's celebration, she brought the phone back against her ear. "Okay. I'll set everything up, and text you the information. His name is Dean by the way!"

"Sounds good. Bye Care!" She quickly hung up the phone before Caroline could squeeze in any last adjustments. She let a huge sigh out and let the phone drop beside her on the mattress.

 _Dean._ She thought. _Let's just hope you're better than the last two._ She smiled at her thought.

As promised, Caroline sent the details of Elena's blind date. A huge sigh of relief escaped from her when she recognized the restaurant that they'd be eating at. She didn't really have it in her to go all out on dressing up, so she picked a maroon, lace dress and a pair of black flats. She wore her long hair in waves and was light with the make-up. Satisfied with her reflection, she grabbed her handbag and phone and head out the door.

Upon arriving at the restaurant she suddenly felt her stomach clench up in nerves. She gripped onto the steering wheel of her car and closed her eyes.

"Calm down, Elena. We got this. We'll go in and try to have a good time." She reassures herself. Once she built her confidence, she nodded and climbed out of the car.

Inside of the restaurant, she lets out a sigh of relief when she takes note that it isn't too busy. If all goes bad, atleast the food will be served quickly, and she get make a run for it before dessert. The hostess notices Elena, eying the seats, trying to find someone.

"Hello," Her perky voice captures Elena's attention. "Welcome to Luigi's. My name is Sara, are you looking for someone or..."

"Hello, Sara. Thank you, um, I'm not sure if he's here yet..." Elena bites her lip for a moment as she tried to remember his name. "Dean Winchester?"

The smile the hostess was wearing quickly fades away when Elena says his name, but is just as a quick to recompose herself. "Yeah, he's here. Follow me." She says, forcing her smile back on. Sara leads Elena down an aisle of booths; closer towards the end of the restaurant.

When they reach the final booth, Sara speaks. "Mr. Winchester..." She begins.

"Just can't stay away, can you?" Elena hears a deep, teasing voice respond.

Sara chuckles and shakes her head. "Your uh," She moves aside to expose Elena. " _date_." Elena feels her face scrunch up in confusion by the tone in which Sara said the word " _date_ ". Did she hint jealousy?

"Oh," Dean quickly gets up from his seat, his eyes wide and set on Elena. "Wow," He breathes out. "I guess Caroline wasn't being over dramatic about you after all," He teases; shooting Elena a wink as he extends out his hand to her. "I'm Dean."

Elena feels the heat rush up to her cheeks. She reaches out and grips his hand. "I'm Elena." She responds with a smile. He gives their hands a firm shake, before gesturing for her to sit. Elena silently thanks him, and slides into her seat. Dean does the same taking his place back on the opposite side keeping his eyes on Elena, a small smile growing on his lips as he noticed how nervous she was.

"Your waiter will be with you shortly." Sara says, trying to get Dean's attention back on her.

Dean looks up at her. "Thanks, sweetheart." He waves her off and turns back to Elena. Once Sara was gone, Dean spoke again. "So, Lena... may I call you Lena?"

Elena pulled her eyes away from the menu, to look back at her date. She hated to admit that Caroline had been right on one thing so far... The Winchester gene pool was in fact very generous. "I don't mind." She smiles at him.

"So, Lena," He smirks. "How is it that a girl like you needs help from a friend to land a guy?"

She narrows her eyes. "What do you mean a 'girl like me?"

"Oh come on," He lifts his brow. "You can't honestly tell me you don't know what I mean..."

She shrugs and shakes her head.

He rolls his eyes. "Okay, okay. Let's see then..." He crosses his arms, and leans back in his seat. His eyes narrow as he scans her, trying to figure out her flaw. "You've got brains... Or so Sammy says. You're a med student, right?" She nods in response. "You've got looks... Personality; you don't seem like you're the psycho type."

"What exactly are you doing?" She questions, suddenly feeling very uncomfortable.

"Trying to figure out why the last idiot you dated let you go." He quickly responded.

She chuckled. "If that's your way of asking about my last relationship, my answer is; people grow up and apart."

"Ah, so in other words you got bored of him?" He accuses.

She narrows her eyes at him, feeling a little offended by his accusation. She mirrors his posture, by crossing her arms and leaning back in her seat as well. "I'm done talking about _my_ past. Your turn Mr. Casanova, what about _your_ past?"

"Casanova, huh?" He lifts his brows, impressed by how quickly she reacted.

"Don't think I didn't notice how Sara," Elena gestures with her head. "was drooling over you. She probably stabbed me in her thoughts atleast 100 times on our walk from the entrance to here."

"Fair enough," He chuckles. "Well, you're not getting information about my past, sweetheart. Sorry." He says, sitting back up and bringing his menu up.

"Fine. Then mine is off limits too." She once again mirrors his actions, and begins reading over the menu.

The rest of the dinner went relatively well. Dean was quite a flirt, and Elena found herself enjoying it. Once they both finished their dinners, they decided to share a chocolate cake.

"How can a restaurant not have pie?" Dean slides his fork down the cake, and grabs a chunk.

"Because not everyone has a crazy fetish for it like you, Dean," Elena responds, before shoving a piece of it in her mouth. Dean lifts his brow at her. Suddenly feeling very self-conscious she covers her mouth. "What?" She questions with a full mouth.

"Speaking of fetishes..." He says as he slowly slides the fork down the cake, and seductively takes another piece and puts it in his mouth.

She rolls her eyes. "What about them?" She questions, now reaching again for another bite.

"You gonna show me any of your little secret kinks tonight?" He lifts his brows. She scoffs as she puts in a piece of cake in her mouth. She prepares a witty remark to respond, but stops as soon as she meets his eyes; realizing he was serious.

"Wait, are you serious?" She asks.

Dean grabs the final piece of cake and shoves it in his mouth. He nods at her question. "I was thinking if you don't want to go back to your place, we could get a hotel room," His implication hitting Elena like a slap to her face.

"Thanks for dinner," She didn't let him finish speaking, quickly grabbing her handbag and sliding out of her booth.

Dean raised his hands in confusion by her sudden reaction. He got out of his own seat, quickly pulled out his wallet and a few bills; tossing them onto the table. He followed her, calling out after her.

Once she stopped at her car, Dean put his hand on the driver's door to prevent her from getting in. She turns to face him.

"What do you want?" She asks angrily.

"What the hell, Lena? What got your panties twisted in a bunch?"

She rolls her eyes. "My panties aren't twisted," She lets out a frustrated sigh and stomps her foot. "Can you move, please?"

"Not until you tell me what the hell just happened? I thought we were having a good time..."

She turns to face him, eyes narrowed, jaw set. "We were having a good time, Dean. Until you basically ask me where I'm going to have sex with you? I'm not a sex on the first date type of girl, and," Elena points a finger at him. "the fact that you think I'm that person is just a slap across my face."

Dean lifts his hands defensively. "Listen, sweetheart. I ain't the dating type. You, yourself accused me of being "Mr. Casanova."

Her eyes go wide. "I was kidding, Dean! If you're not the dating type, then why the hell did you agree to a blind DATE?" She shouts.

"Caroline said you'd been out of the game for a while. She said I was perfect to get your mind off of your ex... I figured..."

Elena's hand flew up to her mouth as the heat from embarrassment began to rise in her cheeks. "Oh my god. She set me up for a one night stand!" Dean begins to laugh, which causes Elena to narrow her eyes him again. "Shut up." She says, before pushing him out of her way. She opens the car door, and climbs in. Dean walks away, shaking his head while laughing, which only builds up the fury Elena was feeling in her chest. Caroline was going to get an earful when Elena got home.

Elena found herself outside of a friend's apartment. She needed to sulk, and he was the only person she felt she could talk to lately. So she knocked on the door. A couple of moments later, she began to hear the sounds of bolts unlocking. When the final bolt unlatches, he pulls the door open to expose those deeply concerned blue eyes. His dark hair was disheveled and he was wearing a t-shirt and pajama pants. She had woken him up.

"Elena, what's wrong? What are you..."

She invites herself into his apartment. "Cas, I know it's late. I'm sorry, I just... I needed somewhere to cool down. I was hoping..."  
"Oh, yes. Of course, Elena. Make yourself at home," He gestures towards his couch. "I'll go get somethings for you to sleep." He makes his way into his room, grabs a blanket and a couple of pillows. When he returns to the living room, he finds her sitting on the couch. He hands her the items.

"Thanks, Cas." She smiles at him. He smiles back, and then notes the clothes she'd been wearing. He quickly made the assumption, it had been another date gone bad.

"I'll get you something of mine so you can get out of those..." He clears his throat suddenly uncomfortable at the thought of Elena undressing.

"Thanks again, Cas." She says. He nods and makes his way back into his room.

The next morning Cas had made breakfast for the both of them. Elena told him everything from the date, and he listened to every word; occasionally giving his opinions on the situation.

"It was bad, Cas. And I over reacted. I probably seemed like this stuck up prude." She stabs a sausage that was on her plate.

"Don't worry about it, Elena. It's not like you'll ever see him again right? Doesn't he live in Kansas?" Cas asks.

"You know you're so right! He's only visiting, Sam and Caroline for a while. He'll be leaving soon, and we can all forget about this, right?" She smiles. Cas nods in response. "Thank you for listening, Cas. You're seriously the best!" She exclaims, and gets up from her seat, to give Cas a kiss on his cheek. "I gotta get home, I have class in a couple hours. I'll talk to you later, Cas!"

"My pleasure." He responds, as she quickly runs out of his apartment, leaving him behind with her half eaten meal.


	2. Second

3 Weeks Later

The incident with Dean had been almost completely forgotten. Elena was quick to forgive Caroline for setting her up on that blind date, and was ultimately forbidden in meddling with Elena's love life. Instead Elena focused on her school. She was a med student, and that meant her attention was devoured completely by her classes. Tonight being a Friday evening meant nothing to her anymore. She sat on her bed, with books scattered all around her. She was so engulfed in her studies; she barely heard the pounding that was coming from her apartment door.

"ELENA! OPEN UP!" She heard Caroline's muffled voice as she approached the door. She smiled and shook her head at her friend's impatience once she began to unlock all of the bolts. The door almost hit Elena in her face when she reached the final one; as Caroline's impatience drove her to opening the door herself. "God, you take so long!" She says as she invites herself in.

"Hi to you too, Care," Elena responds with a quick roll of the eyes. She quickly begins to lock up all the bolts before turning her attention back to Caroline. "So what's…" She stops mid-sentence now looking at her friend. The young blonde had a huge smile spread across her face, with her hand stretched out towards Elena. She looked at the hand, and quickly spotted the item being shown to her. "Oh my god, Care…" Her smile was now mirroring Caroline's. "Congratulations!" She pulls her friend who was on the verge of tears into a huge hug.

"Thank you!" Caroline squeezes Elena, and pulls away. "Can you believe it? I'm engaged!" She squeals in excitement. The two take a moment to cheer excitedly.

After the initial shock of the news; Elena quickly fixed up a batch of hot cocoa to celebrate the news. The two friends were now sitting in Elena's living room with their mugs in their hands.

"It's the middle of spring and we're drinking hot chocolate. Are we delusional?" Caroline teases.

"It's the only thing I could make under such short notice," Elena rolled her eyes. "My fridge isn't exactly stocked at the moment."

"Well, doesn't matter," Caroline takes a sip from her mug. "It definitely hits the spot." She smiles.

"So, tell me! How'd he propose?"

"Well," She places her mug on Elena's coffee table. "It wasn't anything extravagant. You know, Sam; he's very traditional," Elena nods in understanding. "We were eating at that Italian restaurant, Luigi's…" Elena held back the urge to roll her eyes at the mention of the restaurant. "And just after dessert, he grabbed my hands. He began telling me how much I meant to him, and it didn't take long for me to put together what he was about to do. He got up from his seat, and got down on one knee in front of me."

"Aww, Care," Elena wipes a tear she hadn't noticed had escaped from her eye. "I'm so happy for you guys!" Elena pulls her in for another hug.

"Thank you, Elena."

"So when are you guys planning to have the wedding?" Elena asks, once they pull away from each other.

"I want a Fall wedding, Sam wants Winter. Speaking of the wedding," Caroline quickly reaches for her mug of hot cocoa. "I was hoping you wouldn't mind being my maid of honor!" She exclaims excitedly.

"Oh my god, of course Caro…" Elena pauses for a moment. "Wait… who would be Sam's best man?" Elena narrows her eyes at Caroline. Caroline forces a big smile, confirming to Elena it's exactly who she thought it would be. She throws her head back and lets out a loud groan. "You can't be serious Care!"

"I know, I know. I'm sorry, Elena. But he's Sam's brother, I can't exactly say no. But we promise we'll make sure he's on his best behavior. Please, Elena." She begs.

Elena takes her lip between her teeth. Caroline was her best friend. She couldn't let her down on something this huge. "Care," She begins. Elena's tone of voice tells Caroline to prepare herself to be let down. "I would love to be your maid of honor." She smiles at her friend.

Caroline squeals in excitement. "Yes! Oh my god, you totally got me there for a minute." She says as she leans over and pulls Elena in for a hug. "This will be so much fun, Elena!" Caroline lifts herself off of the couch and grabs her handbag.

"Wait, what? You're leaving already, Care?"

"Yeah, I'm sorry. I just may have/kind of ran out on Sam after he proposed and came here," She admits guiltily. Elena chuckles and shakes her head at Caroline. "I'll call you tomorrow. We got to get started on wedding duties!" She says as she runs out the door.

Once Caroline was gone, Elena slumps back on her couch. Her hands fly up to her face as a loud sigh escapes from her mouth. She was thrilled for her best friend, but she dreaded having to face Dean again. The next few months were going to be torturous when it came to dealing with him, but she was going to deal with him nonetheless. She was going to be the bigger person, hold her head high and kill him with kindness. Yes, that's exactly what she was going to do.

Time flew by quickly as the big day approached. Caroline's neuroticism and perfectionism pretty much pushed her to being her own maid of honor, as she handled every single detail of the wedding; not fully trusting Elena. Elena knew better than to interfere with Caroline's preparations though, she was present at any moment Caroline needed her, and was there to calm her down whenever something might have gone awry. Lucky for Elena, she saw very little of Dean. Their interactions were short and usually supervised by either Caroline or Sam. The engaged pair would quickly intervene when they'd begin to see Dean and Elena beginning to bicker.

The big day came, and everything in the ceremony went flawlessly. Tears threatened to escape from Elena's eyes once she saw Caroline walking down the aisle, but were quick to fall once her attention landed on the look on Sam's face. The way he looked at Caroline, the love he held in his eyes for her. That was the moment Elena knew for sure, Sam would take care of Caroline like no other. She even felt a quick pang of jealousy. She began to hope that one day, someone would look at her the way Sam was looking at Caroline as she walked down the aisle.

Laughter and tears were shed as Care and Sam exchanged their vows. Family members in the audience cheered for the newlyweds and then came the reception. Elena looked out at the audience, and took note of the small crowd they were surrounded with; the small crowd who were now all joined as a big family. Her attention went back to the newlyweds, the smiles on their faces after they shared their first kiss as an officially married couple. And right behind, the couple, Elena spotted Dean. She hadn't paid any attention to him throughout the entire ceremony. Surprise filled her when she noted his glistening green eyes, the happiness Dean held for his younger brother. Surprisingly enough a small smile grows on her lips as she kept her gaze on Dean's expression.

Dean felt the sensation of being watched. He peeled his eyes away from his younger brother and his new wife to find the culprit. He quickly found the pair of doe eyes that were glued on him. He shot her back a wink once she noticed he had been looking back at her. She rolled her eyes at him and began to make her way to congratulate Sam and Caroline. Dean chuckled and followed her lead.

The battles were constant between the two as another couple years flew by. Dean had officially moved to be close to his younger brother, and being Caroline's best friend meant Elena was constantly bumping into Caroline's brother in law. Dean knew just what buttons to push to irk her. A lift of his brow would earn him her death stare, a wink would earn him a roll of the eyes, a suggestive remark would earn him a scoff; these little, mischievous back and forth battles were what made the _many_ events Caroline planned bearable for Dean. And there were many events planned throughout the year. Besides the obvious holiday season, Caroline practically threw some sort event of get together each month; from Christmas to celebrating their dog's birthday.

July was closing in, and one of Caroline's favorite holidays was approaching. Something about fireworks on the Fourth of July always seemed to bring Caroline an extra amount of joy. She was sitting in the kitchen with her eyes glued on the laptop screen, when Sam walked into the house. She was so focused on her research; she hadn't even heard Riot, their dog, bark at him when he came into the house.

"It's a good thing we got Riot," He says walking into the kitchen. She peels her eyes away from the laptop and looks up at him questioningly. "A burglar could have come in, took all of our things, and you wouldn't have noticed unless he tried taking the laptop from you," He teased. She rolled her eyes at him and chuckled; before he leaned down to give her a quick kiss. "What are you doing anyway? Aren't you done with classes for the summer?" He asks as he shrugs out of his coat.

She points at the calendar hanging on the kitchen wall. "It's almost July, Sam. Yes. I'm on summer break. That being said, with the 4th coming up soon; I'm looking for a beach house for us to rent for a few days." She winks at him.

He chuckles. "That sounds nice," He leans over her shoulder to get a look at the screen, checking out some of the options. That's when he notices the settings, Caroline had preset. "2 rooms?" He questions. "Are you planning on sleeping in separate rooms?" He takes a seat beside her. His eyes remain glued on her, as she avoided his question. "Care, what are you up to?" He asks with his skeptical tone. She looks up at him and gives him her guilty look. He knew exactly what she was plotting.

He lets out an exasperated sigh. "Come on, Care. Am I really that boring of husband, that you need to interfere with Dean and Elena?"

"No!" She exclaims. "Sam you're the best husband I could have ever asked for," She leans over and gives him a quick kiss. "And because you're the best, you're going to help me, help them." She smiles.

He smiles at her and shakes his head. "Babe, anytime those two are together, I'm afraid we'll end up having to call 911 for help. They don't like each other, Care. What makes you think you can change that?"

"Because they don't _hate_ each other, Sam." He tilts his head puzzled. She lets out a sigh and begins to explain. "If they _hated_ each other, they would do everything in their possible ability, to avoid being within a mile of each other. Yet, at every event we invite them to, they always find each other. They clearly look forward to seeing one another."

"Okay, so they don't hate each other. Doesn't change the fact that Elena doesn't want you to interfere with her relationships. Plus isn't she dating that guy Castiel?" Sam leans back in his seat, and crosses his arms. She lets out a disgusted sound. "What you don't like him? I think he's really nice." Sam says.

"Yeah, exactly what I think!" She exclaims.

Sam chuckles at her reaction. "Wait, so you think he's nice, but you don't like him?"

She groans. "How you're a lawyer, I will never understand," She teases. "First of all, they're not dating-"

"But you said," She lifts her finger to quiet him.

"I said I had a feeling he had a thing for her. Anyway, a relationship needs balance to work. Cas is nice. He's super nice, just like Elena. Nice and nice. You'd think that'd be a good match, but it isn't. Nice and nice make for a boring relationship."  
"So you're saying Elena needs a bad guy?"

"No! She just needs a nice guy, who has a little bit of a bad in him to make their relationship exciting." She winks.

Sam narrows his eyes at her and begins to smile. "Are you saying you think I'm bad?" He lifts his brows at her.

She smiles at him, refrains herself from telling him he's the sweetest guy she's ever met and that she's pretty sure she was the one with the bad bone. Instead she turns her laptop, distracting him from his question with one of her own. "So what do you say we invite them on this trip? 4 days, on the beach. Could make for an interesting 4th of July weekend." She lifts her brows.

He lets out a sigh. "If you get caught. I'm not going down with you," He starts. "My only part in this will be to get Dean to agree to coming on this trip with us."

"Fine, that's all I need." She says, before leaning forward and giving him a thankful kiss.


	3. Third

Convincing Elena to come on the trip wasn't as hard as Caroline thought. Of course, Caroline may have left out a detail or two, but who was keeping count right? Elena sat in the back seat, staring out the window while Sam and Caroline conversed in the front. She tuned out the conversation between the young couple as she enjoyed the changing scenes from her window. They were long gone from urban scenery and had hit a long rural road. She watched with pure glee whenever they'd drive by a farm that contained cattle.

They'd been driving through the countryside for a little over an hour. At this point the scene once again began to change. The green from the grass was dissipating, and sandy grounds replaced it. She opened her window, and let the salty sea air enter her nostrils as she took in a large breath. She resisted the urge to put her entire head out the window to take in the newest scene. They still had a bit of driving to go, but they had arrived. White sand practically glistened as the sun shone on it. The blue of the not so distant sea was mesmerizing.

"This is so beautiful," She says.

"It's nice, huh?" Sam responds. "My parents would always take Dean and me to the beach in the summer, when we were younger. When I moved down here, I began to miss those family trips," He began to explain.

"That's where I come in," Caroline interrupts. "The moment he told me about his family trips-"

"She looked up the best beach closest to Virginia. Of course I didn't know she was doing this-"

"So I kidnapped him." Caroline says smugly.

Elena laughs. "How exactly did you manage to kidnap a giant?"

"She actually roofied me." Sam says with a hint of embarrassment in his voice. Elena's jaw drops at Sam's confession. She looks at Caroline, judgement in her eyes.

"Hey, hey!" Caroline exclaims. "It's not like he would have accepted to go with me if I just asked okay. He would have come up with a lame excuse to put off the trip. 'I got a test on Monday' kind of stuff."

"But I did have a test!" Sam exclaims.

"That's beside the point," She retorts. Sam rolls his eyes and turns his attention back to the road. "The point is I didn't have another way to get him to stay quiet for the long drive. And in the end, we had a fun trip." Caroline reaches over and takes Sam's hand in hers. He then faces her, and returns the smile she'd been giving him.

"Yeah, I guess so." He responds, giving her hand a small squeeze. Elena smiled at the small gesture between the two, before she turns her attention back out the window.

The sea air filled her lungs once again, and she felt at peace. _This trip was a great idea._ She thought. _Nothing could go wrong_.

She soon found out she'd spoken too soon. When the three pulled up to the beach house, a figure that'd been sitting on the porch lifted himself up to his feet when he saw them. Elena had to do a double take when she spotted him. With her jaw dropped she turned to face Caroline.

Sam spotted Elena's reaction from the rear view mirror. "And that's my cue." He said, and quickly climbed out of the car. Caroline followed suit. She avoided eye contact with Elena as she quickly climbed out as well. Elena let out an annoyed breath of air, and she too angrily climbed out of the vehicle.

She then made her way over to Caroline's side before she could get too far. With her arms crossed across her chest, she narrows her eyes at the blonde.

"Caroline, what are you up to?"

Caroline acts baffled. "What do you mean, Elena?"

"Don't play dumb, Care. What are you up to?"

She shrugs. "Sorry, I don't know what you're talking about, Elena."

"Fine, I'll go ask Sam then." Elena drops her arms and begins to make her way to Sam. Caroline quickly grabs her by her arm.

"No, stop!" she exclaims.

"Spit it out, Care. Why didn't you tell me Dean was going to be here too?" Elena questions.

"Would you have agreed to come if I told you he was?" Caroline questions back.

"That's not fair."

"It's 4 days, Elena. We're on the beach for 4 days. Are you seriously telling me you're only looking at the downside here?"

Elena lets out a defeated sigh. "No, I guess not. But, Care…"

"No 'buts', Elena. 4 days! You can survive 4 days. Then when we return you can go back to hating him."

Elena rolls her eyes. "Fine." She says grumpily.

Caroline clasps her hands together in excitement. "Great! Now let's get unloaded." Caroline grabs Elena by her arm, and drags her to the back of the car. She opens up the trunk door, to expose their entire luggage. Elena's eyes widen at the amount of luggage that was stuffed in the trunk.

"Care it's 4 days… What is with all the bags?" She questions.

The blonde shrugs. "I couldn't decide what to bring, so I brought options." She says, as she reaches in and attempts to pull one out. Caroline's struggling grunts catches Sam's attention. He quickly makes his way to help her out, with Dean a few paces behind.

"Babe," Sam puts his hand on Caroline's shoulder. "I'll get them." He says smiling at her.

"You sure?" She questions. He nods in response and begins to pull out the bags. Feeling satisfied with Sam's response. Caroline turns to Elena, only to find her scowling at Dean as he gave her a smug smile. Caroline let out a sigh and took a few steps towards the two.

"What's going on?" She asks Elena. The scowl is then aimed at her.

"We have to share the room, Care? Really?" Elena asks.

 _This was going to be a long 4 days._

After the 4 of them unpacked and settled themselves into the beach house. They decided it was time to hit the actual beach. Sam and Caroline walked hand in hand, as they led Dean and Elena down the boardwalk. Elena watched with amusement as the two playfully swung their hands as they walked.

"It's like a chick flick in real life." Dean suddenly remarks, pulling Elena away from her thoughts.

She looks over at Dean. "And what's wrong with that? I think it's cute." She responds.

"Of course you do." He chuckles.

She narrows her eyes at him, and opens her mouth to speak. She then closes it again, deciding against speaking up; not wanting to bicker with him again.

"Okay, you know what," She stops walking. Dean stops as well and looks at her curiously. "We're going to be here for 4 days. I'm a med student, and my stress is practically pouring out of my ears. This trip is my only escape and I really want to enjoy it,"

"Okay." He says.

"So, what do you say we both wave the white flag and put a halt to our fights? Atleast until we get back home."

"Sweetheart, you're the one who starts the fights," He notes. "But yeah, okay. Sounds good to me." He extends his hand out to her.

"Good," She says, reaching her hand out and gripping his. "I don't _always_ start them." She mutters as they shake hands.

He laughs as he drapes his arm around her. "Sure, whatever you say, sweetheart." Surprisingly enough, Elena doesn't push him away. The two then begin to follow Sam and Caroline once again who now, were a quite a distance away.

Once on the beach, Elena lays out her towel on the sand. She tosses the book she brought along with her onto the ground and then begins to unbutton her shorts. Feeling a pair of eyes on her as she removed her shorts, she quickly turned to face the culprit.

Dean sat beside her, with his brows lifted and a smug smile on his face. Elena rolls her eyes.

"Stop it." She demands.

He raises his hands in defense. "What? I'm not doing anything, sweetheart. Just enjoying the view." He teases. She once again rolls her eyes and laughs.

"You are such a perv." She accuses, sliding her shorts down and kicking them off to the side. She reaches to remove her shirt, but once again feels Dean's gaze on her. "Dean please," She pleads.

He chuckles. "Fine." He removes his eyes off of her, and looks out to the beach. He watches the waves crash onto the shore, the kids splash in the ocean. His attention is then pulled by the sound of squealing. He spots Caroline and Sam, happily splashing at each other in the water. His lips curl up into a smile, seeing the happiness his younger brother had with his wife.

"Oh crap!" Elena's voice says beside him. He turns his attention back to her. She'd removed her t-shirt now, and was now only in her bathing suit. Dean bit his tongue, knowing it would be best not to make any more suggestive comments on her appearance; instead he focused on her problem at hand.

"What's wrong?" He questions.

"I left my phone at home," She says a she searched through her beach bag.

"What, you need to take a 'Hashtag beach selfie?" He jokes.

She narrows her eyes at him. "No. I was going to use the timer to get an even tan."

He laughs, and digs into his pocket. He grabs his own phone and hands it to her. "There ya go, sweetheart."

She takes it reluctantly from his hands. "Are you sure?" She asks. He simply nods and returns his gaze onto the beach.

Surprised by the gesture, she feels her eyes linger on him a moment longer than need be. She clears her throat and begins to set the timer.

"Thank you." She says, as she lies down and opens up her book.

Her eyes stared at the words, but her mind didn't register the words. Having Dean so close beside her, for the first time she felt intimidated, a little self-conscious. Realizing it was pointless for her to keep reading; she shuts her book and sits up. Dean turns to face her, surprised by her sudden action.

"What's wrong?" He asks.

"I'm too distracted," She says. He tilts his head curiously. "The seagulls… I don't know. I can't focus on my book," He nods in understanding, and once again turns his attention back to the beach. "Want to go for a walk?" She asks, pulling his attention back to her.

Baffled by her question, Dean is left speechless. Suddenly the heat in her cheeks begin to rise.

"Or not. I, um… I'm gonna go… " She says as she quickly gets up from the towel and avoids eye contact with him as she frantically began putting back on her clothes.

 _You idiot!_ _Why'd you ask that, Elena? What are you doing?_ She mentally scolds herself.

He gets up from his chair, and grips her arms to hold her steady. "Yeah, let's go for a walk." He says smiling at her.

"You don't have to…"

"No it's okay, I saw a funnel cake place on our way here. We can share one." He says.

She nods and returns his smile. "Yeah, okay let's go." She responds.

The two then begin to make their way back to the boardwalk, in search of the funnel cake place. The conversation seemingly flowed between the two the more time they spent with each other. Once they arrived at the Funnel Cake Shop, Dean ordered one for the both of them. They took their cake, to an empty table with two chairs on the boardwalk.

The conversation continued as they ate. At one point Elena found herself stunned at the man who sat in front of her. He wore Dean's face, but it wasn't the same man she'd been bickering with over the last few years. It was the Dean she met on her first date. The little hint of Dean, she saw staring at his younger brother with tears in his eyes, on his wedding day.

This was a different Dean, and she liked him.


	4. Fourth

Elena tossed and turned as she tried to find a comfortable spot on her bed. When she woke, her eyes went directly to the window. The lack of sunlight let her know it was just before dawn. Light snoring emitted from the bed beside her and caught her attention. She glared at a peaceful Dean with jealousy as he slept soundly.

Knowing it was now pointless for her to keep trying to go back to sleep, she lifted herself off of her bed. She quietly tip-toed as she navigated her way around the room to reach her bag. Once she got to her bag, she bent down, and unzipped it slowly; still being careful about making noise. She shuffled through the contents, looking for a suitable pair of shorts and a tank top to change into.

Her hard work almost a complete success, up until she got back up on her feet. Spotting her shoes across the room, she then began to make her way over to them, only to stub her toe against the foot of Dean's bed. Her free hand flew up to cover her mouth from spouting the string of obscenities she'd conjured up.

His eyes flew open when he felt the minor thud against his bed. He lifted himself off of his pillow, and looked down to the location of the impact. His eyes land on Elena, with her eyes clamped shut and hand covering her mouth.

"Lena?" He asks. She opens up her eyes and meets Dean's sleepy gaze. "Are you okay?"

She wipes a sneaky tear that had escaped from her eye and lets out a sigh.  
"Yeah, i'm fine. I just stubbed my toe against your bed." She explains.

He chuckles. His eyes then travel to the window. "What are you doing sneaking around the room at this time?"

"I woke up," she shrugs. "and I could 't go back to sleep. I figured I'd might as well go out for a walk."

He nods in understanding. "Sounds good, I'll come along." He says as he starts lifting himself off of his bed.

"No, no! Go back to sleep. I didn't mean to wake you." She says apologetically.

"It's fine, Lena. I couldn't go back to sleep now if I wanted to." He says as he slipped into his shoes.

"Okay..." She says. "I'll go change and then we can get going, I guess." She says. She turns to exit the room when Dean shouts out her name. She stops abruptly and turns to face him, puzzled by his outburst.  
"What is it?"

"You can always change in here." He lifts his brows at her suggestively.

She rolls her eyes and scoffs. "You wish." She laughs then continues to make her way to the bathroom.

After Elena switched out of her night clothes, the two were soon out and enjoying the sights and sounds of their surroundings as they walked side by side. Small talk topics exchanged between the two, not leaving room for any awkward silences. About a mile and a half into their walk, Dean spotted a small diner. He suggested the two of them get some breakfast. Elena agreed, and they quickly made their way to the diner.

Upon arrival the first thing Elena noticed was the atmosphere. The diner was small and humble. From the looks of it, it was family owned. A short blonde woman; probably in her 30's, grabbed their attention once they walked in.

"Good mornin'!" She exclaims with a beaming smile spread across her face.

"Good morning." Both Dean and Elena greet her in unison.

"Will it just be the two of ya?" She asks. They both nod. She quickly bends down to grab a couple of menus and gestures for them to follow her. She then hands them their menus as they take their seats across from one another.

"What can I get ya two lovebirds to drink?" She asks.

Elena's eyes grow wide. "Lovebirds," she chokes out. "We're not..." Heat begins to rise in her cheeks as she begins to explain. Dean quickly jumps in. Elena relaxes a bit, thinking he'd handle the situation but to her horror, those were not his intentions.

"Oh, come on, sweetheart. Don't be so modest." He winks at Elena, then focuses his attention back to the waitress. "We'll take 2 coffee's darling." He orders.  
The waitress nods her head  
"I'll be right back with those two cups of joe." She says and quickly scurries away once she notes the unamused expression on Elena's face.

Dean then focuses his attention back to Elena; he chuckles upon seeing her narrowed eyes.  
"What's wrong, sweetheart?" He asks.

"I thought you were going go help me! Now she thinks we're together." She responds, the annoyance in her tone clear.

"So what? It's not like we'll see her again. Besides, what's wrong with her _thinking_ you have me as a boyfriend? I'm a catch." He smirks and opens up his menu.

"A catch huh? So what, you think you got the entire package?" She asks.

Dean doesn't peel his eyes away from the menu.  
"Yep."

She scoffs and rolls her eyes at his response. She then opens up her menu and begins to scan through the items as well.

Pancakes, eggs, bacon and sausage; the perfect breakfast meal was quickly scarfed down. Elena leaned back in her seat, slowly beginning to regret her choice in upgrading her meals for a dollar more. She looked across from her where Dean was digging into his third batch of pancakes.

The site of Dean's food made Elena groan from the fullness she felt. Instead, to keep her mind off of what was in front of her, she began to focus on Dean's face. It was true, the older Winchester was quite a catch; physically speaking. She couldn't deny the fact that he was pretty easy on her eyes. But it then occurred to her, she didn't really know anything about the man. She realized she'd been too busy bickering back and forth with the man, that she _never_ actually got any details from him, from his life.

Dean felt Elena's eyes on him as he ate. Suddenly feeling self-conscious; he wiped his mouth with his napkin. His new action causing Elena to realize how long she'd been staring. It didn't take long for Dean to note the slight embarrassment the brunette held at being caught.

"You know Lena, the offer from our first date still stands." He winks at her.

She rolls her eyes and sits up straight in her seat. "Thanks, but no thanks. I've had enough pig for one day." She winks back.

His hand flies over his heart dramatically. "Ouch." He says, the sarcasm obvious in his tone. He chuckles and waves off her comment. "What's on your mine then?" He asks.

She bites her lip for a moment. She had conjured up a certain amount of curiosity in learning more about Dean.  
"Alright," she begins. She clasps her hands together and places them on the table. "So you claim you're a 'catch' right?" He smiles, but nods. "What makes you think you are?" She asks.

"I was joking, sweetheart. You already know I don't do the whole dating thing."

"Yeah, okay. But for the fun of it and my own curiosity; besides your physical appearance what would you have to offer if we were in a relationship?"

"Physical appearance huh?" He lifts his brows at her suggestively.

"Dean..." She whines.

"Fine," he laughs. He takes a moment to think of an answer to her question. "Sex." He responds.

She shakes her head. "Besides that." She pushes.

Dean groans. "I don't know, Lena. I don't _do_ relationships."

"Why not?

"Why do you care?" He retorts his annoyance beginning to rise.

"Just trying to figure you out; that's all." She admits.

"Nothing to figure out, sweetheart," he digs into his pocket and pulls out his wallet. "What you see is what you get." He says as he pulls out a few bills and tosses them on the table. He then abruptly gets up from his seat and makes his way out of the diner; leaving Elena behind wondering, _what the hell just happened_?

By the time Elena had gone outside the diner to find Dean, he had been nowhere in sight. Figuring he'd made his way back to the house, she did the same.

Once she arrived at the house, Sam and Caroline were seemingly just getting out of bed.

"Elena?" Caroline asks, surprised to see Elena entering the house. "Where'd you go? We didn't even notice you weren't home." She says.

"I woke up and couldn't go back to sleep," Elena responds briskly. "Hey, have either of you seen Dean by any chance?" She asks.

Sam's eyes widen. "I'm surprised to hear he was awake before noon," he laughs. "But no, we havent. Why?"

Elena shakes her head. "It's nothing." She says "I'm going to take a little nap, guys." And with that she heads up the stairs. Sam and Caroline exchange looks before shrugging off Elena's question and continued with their morning routine.

Elena half expected Dean to be in his bed when she entered the room. She was surprised when she even felt slightly disappointed to not find him there.  
-

A couple hours and a pillow to the face; Elena is awoken. She flings the pillow away from her and sits up in her bed.

"What the hell?" She questions angrily as she wipes her eyes to regain her vision.

"I need your help!" Caroline whines.

"What is it, Care?"

"Well," Caroline breathes out. "Apparently, Sam told his parents we were going to be out here, and to make the long story short they just showed up at the door with Dean." Caroline says frantically.

"So what, Care? They're your in-laws." Elena responds, as she lifts herself off of her bed. She grabs an elastic hair band and ties her hair up into a ponytail.

"I know that, Elena. But I've never really spent one on one time with Sam's mom. You know more than anyone else I tend to have no filter when it comes to talking and I _really_ don't want to put my foot in my mouth. I just need you to supervise. That's all."

Elena sighs. "Fine." She says. Caroline jumps gleefully and grabs Elena's hand. She drags her along as she descends the stairs to join the rest of the Winchester clan. She leads her out the backdoor to the backyard area.

The boys were sitting and chatting with their parents, when Elena and Caroline showed up. All eyes turned to them when Caroline slid the backdoor open.

"I got her!" Caroline announces upon arrival.  
Elena smiles at the new guests, but it quickly fades when she makes brief eye contact with Dean. He turns away from her and focuses on his beer. As they approach the picnic table, both John and Mary get up from their seats.

"Hello, Elena." John extends his hand out to her. Once she grips it, he gives her a firm shake.

"Hello, Mr. Winchester." She smiles at him, then turns her attention to the smaller blonde woman beside him.

She approaches Elena with her arms wide open.  
"Elena, darling! It's so good to see you again," she says as she pulls Elena into a hug. Elena laughs and returns the hug.

"It's nice to see you too, Mrs. Winchester."

Mary then quickly pulls away from Elena. "'Mrs. Winchester is _so_ formal," She rolls her eyes "Call me Mary, sweetie." She says smiling at her. Elena nods.

"Will do, Mary." Elena responds.

Feeling satisfied, Mary then turns her attention back to the rest of the family.  
"So what's on the schedule for today?" She asks as she looks at everyone for an answer. "Well don't everyone answer at once!" She says sarcastically.

Caroline then quickly chimes in. "Sam and I were thinking about going to the rides on the board walk. We could all do that if you guys want to!" She suggests.

Mary claps her hands together in excitement. "That's a great idea, Caroline. Board walk rides it is!" With no opposition from the family, they all then began to make their way down to the boardwalk.

Wanting to avoid sitting with Dean on any of the rides, Elena made sure Caroline was by her side at all times. Ride after ride, the girls were together. That was until the ferris wheel was brought up. Elena felt slightly betrayed by Caroline when she agreed to go with Sam, but of course she kept it to herself. Just as Elena turns to leave the Ferris Wheel line, another blonde stops her.

"Elena, sweetie," Mary begins. "John swears the Ferris Wheel makes him nauseous, and Dean simply refuses to ride. Will you ride the Ferris Wheel with me?" She asks slightly pouting. Elena can see where Sam got the puppy dog eyes from.

"Of course, Mary." Elena says smiling. And with that, the two get back in line.

As the ride takes them higher, the view of the ocean becomes breath-takingly beautiful. The sun shines off of the water, almost as if there were thousands of diamonds scattered in the deep sea. Elena's eyes are glued to the scene before her.

"You know, John and I met at a beach when were young." Mary says, pulling Elena's attention away from the sea.

"Oh yeah?" Elena asks.

Mary nods her head. "That's why we made it a family tradition to go every summer to the beach. Just a little reminder for me and John," she looks out to the sea. "Watching the boys grow up and play in the sea... It just reminded us, no matter what problems we might have has, our love created those two. And the ocean brought us together." She turns to face Elena. Elena notes the a small tear that had welled up in Mary's eye. "Over 30 years and i'm still as emotional about the sea as I was when I was younger." Mary jokes as she wipes away her tear. Elena chuckles and gently rubs Mary's back.

"Aw, thank you, hon," She smiles at Elena. "You know, i'm so glad Sam found Caroline. You have no idea what a relief it is to a mother to see their son find a good girl."

"Yeah, Care is great. They love each other very much." Elena says in agreement.

"And what about you? Am I looking at my future daughter-in-law?"

Elena laughs. "No. Not unless you have another son," she retorts. From the corner of her eye she sees Mary's smile fade to a frown. It takes her a moment to realize that she had just offended her _son_. "I didn't mean that..." She begins to apologize. Mary quickly lifts her hand to quiet her.

"It's fine, sweetie. I know how my son can be," She sighs. "A mother knows," She says as she turns back to face Elena. "Dean wasn't always the way that he is when it comes to women."

This piqued Elena's interest. "What do you mean?" She asks. "If you don't mind me asking."

"Of course not, sweetie," She begins. "You see, Dean had been in a pretty serious relationship a few years back. A girl from high-school. She was truly a doll, but they definitely seemed to clash. Dean never really spoke to us about what happened between them, so we got what we could from Sam. From our understanding, Lisa was ready to put down roots, begin a family. Where as Dean wasn't ready for that. Needless to say, the relationship grew colder after a while. Eventually Lisa just left him." Elena took in the information Mary spout out.

She'd already figured Dean had been in a relationship that screwed him up, but she never thought it would hit close to home. Elena's relationship with Damon ended the same way. He didn't want to wait 8 years for Elena. He didn't want to come home at night, and find her too busy with homework to show him any affection. He begged Elena to drop out; promising he could provide for her. As sweet as the offer was, Elena wasn't that type of woman. She wanted to be her own person. Not only have the ability to provide for herself, but to have a title she could be proud of. Damon tried to be patient with her. But eventually; just like Lisa, Damon's patience wore too thin, and he left.

"Lisa's absence really took a toll on Dean. After that relationship, I guess Dean's been too scared to try again. Don't think he's had a relationship that's lasted more than a night in years," Mary shrugs. "But what can I do? I just have hope that he'll find someone that will make him see that not _all_ relationships are the same."

Elena nods in understanding. Now letting the info she'd just learned sink in. Now she partly understood why Dean was always saying he "didn't do relationships". Now she understood why he had gotten so upset when tried to pry into his past. As strong, and uncaring Dean tried to be; she realized he was still hurting. After all these years, Dean Winchester was still hurting.

Once they'd got off the Ferris Wheel, everyone had grown hungry. The group decided to eat out at a restaurant for dinner. And once dinner was over, John and Mary (on Mary's insistence) made sure the foursome made it home safe.

"Alright kids," Mary pulls the 4 of them in to her arms. "You guys don't stay up too late." She warns.

"Don't worry about them, Mrs. Winchester," Caroline giggles. "I'll make sure everyone is in bed at a reasonable hour." She lifts her brows menacingly at Sam; which causes him to do a double take. Caroline then winks and nudges him playfully.

"Caroline, please. Call me Mary," She says grabbing Caroline's attention. "But i'm glad to hear that _someone_ is taking the reign." She shoots another warning look at her sons.

"Alright, Mary. Stop scaring them," John gently pulls his wife back. "We'll see you guys tomorrow for the barbecue." He says as he waves and begins to walk away, dragging Mary along with him.

Mary turns around and shouts out, "Good night, kids! Don't forget to brush and floss!" while still being pulled away by John.

Once they enter the house, Sam announces that he's tired and was ready for bed. He then makes eye contact with Caroline.

"What? Sam it's..." Caroline begins to speak before he clears his throat. He gives her a look, and she quickly realizes what he meant. "Oh. OH. Yeah," She begins to yawn dramatically. "I'm getting tired too," She says. "We're going to head off to bed." She walks over to Elena and gives her a hug.

"That's fine," Elena says. "I think i'm going to watch a movie for a bit, then I'll head off to bed."

"Sounds good," Care pulls away from her and then pulls Dean into a hug as well. "Don't stay up too late, guys. We got alot of stuff to do tomorrow!"

Dean laughs. "You got it boss. Good night." He says. Sam mimics Caroline's actions, and then the two wave off Elena and Dean.

Once they're out of sight, Elena walks over to the living room. She looks through the pile of movies that were sitting on the table.

"Oh, that's a good one." Dean's voice comes from behind her. Elena turns around surprised by him. She simply lifts up the movie, silently asking if he meant the one she held in her hand. "Yeah. That one." He nods.

Elena shrugs, and gets up from her spot. She walks over to the DVD player, and puts in the movie. To her surprise, when she makes her way back to her spot; Dean is sitting in the spot beside hers. She doesn't say anything as she sits back in her spot.

The two are atleast 30 minutes well into the movie when all of a sudden they hear a scream. Startled by the sound, Dean reaches for the remote and mutes the movie. They wait in the silence for a few minutes before another scream emits from the area right above them. It doesn't take long for them to realize what they were hearing weren't actually screams, but moans.

They exchange looks at the realization. Elena's face cringes in disgust while Dean bursts out in a laugh.

"Aw, come on, Lena. Like you've never heard a couple getting it on."

She rolls her eyes, and takes the remote away from him. "Of course I have, but that doesn't mean I want to hear my _friends_ doing the deed." She the presses the play button and turns the volume up; in hopes that'd drown out the sounds that were emitting from the ceiling. Dean then once again takes the remote away from her, but this time he turns off the t.v.

"What the hell?" She asks angrily.

Dean chuckles. "Come on, I have a better idea," he says as he stands up. He stretches his hand out to her. She looks at it incredulously. "Are you gonna leave me hanging or what, Lena?" He asks. Part of her wanted to respond with; _"like the way you left me this morning_?" But she pushed back that urge and took his hand.

They found themselves walking through the sand on an empty beach. The waves crashing onto the shore were just as beautiful at night as it was during the day. The night was clear, and the stars reflected off of the water.

When Dean stopped walking, Elena looked at him puzzled. He chuckles as he begins to stretch out a blanket he'd brought with him. Elena watches as he quickly makes his way to the ground. He kicks off his shoes, and lies on the blanket, using his hands as a pillow.

"What, are you just gonna stand there and stare at me all night, sweetheart?" He questions her.

She suppresses a witty come back, and quickly joins him on the blanket. Now they both were lying on the sandy ground, staring up at the stars. The only sounds around them were the peaceful crashing of the waves.

"Sorry about this morning," He says.

"It's fine." She responds, without looking at him. He looked down at her, surprised by her simple reaction.

"What? That's it? 'It's fine', that's all you have to say?" He questions.

She shrugs. "I was getting my nose into your business. I get it and it's fine." Dean's eyes look back up at the sky.

"What did she tell you?" He asks, now realizing Elena knew something. He loved his mother, but the woman had trouble keeping these things to herself.

Not having the energy to deny she knew anything, Elena decided to answer honestly. "Not much," She sighs out. "Just that you were hurt."

Once again he looks down at her, surprised by her. "And you don't got a lecture up there for me?"

Elena now meets his gaze for the first time. "Lecture about what?" She questions, puzzled by what he meant.

"You know, the 'not all relationships are the same', 'plenty fish in the sea'. Those types of lectures." He suggests.

She shakes her head. "Nope... "Plenty fish in the sea?" She snorts out. "Dean, I wouldn't be surprised if the majority of those fish weren't already caught and released by you." She teases.

"You know me all too well, sweetheart. Still haven't caught one though." He teases back, and relaxes back into his spot.

"Good luck with your fishin', Winchester." She shoots back as she re-adjusts herself as well.

The two remain side by side for the rest of the night, quietly listening to the waves crashing onto the shore, until sleep takes over.


	5. Fifth

As Sam makes his way out of the shower, he reaches for his towel and wraps it around his waist. As he exits the bathroom, he hears Caroline's voice shouting his name. Alarmed, Sam quickly runs out to find his wife.

"Caroline?! What is it? Where are you?" His booming voice shouts out in response. He's standing out in the hallway, head snapping back and forth as he tried to listen for the direction of her voice. His racing heart begins to calm the moment he sees her exiting Elena and Dean's room, with a scowl on her face and her arms crossed.

"What the hell, Care? I thought you were hurt or something." He breathes out.

She loosens up as she approaches him. "I'm sorry. It's just," She huffs. "Elena and Dean aren't in their room. They said they'd be up bright and early to help us get ready for the barbecue for later."

"Well, they probably just went out for a walk or something. I'm sure they'll turn up soon."

"For their sake, they better." She says with a pout as she makes her way past Sam. Sam shakes his head with a smile as he watches his cranky wife descend the stairs, muttering insults at Dean and Elena with each step she took.

With his arm securely wrapped around her, both Dean and Elena slept soundly through the dawn hours. Sometime during the night, Elena's subconscious mind decided to make use of Dean's chest as a pillow. Her action had startled him awake, but he quickly realized she was fast asleep. After momentarily considering gently shrugging her off of him, he ultimately decided against that option. Instead, he found himself furthering the embrace. He wrapped his own arm around her, pulling her closer towards him and soon after went back to sleep.

This is the scene sitting before Sam's eyes. The couple sleeping soundly on the beach; it brought a small smile on his lips as he took in their position. A part of him didn't want to ruin it, but he knew he'd get an earful if he didn't return with the two.

"Did you guys really sleep out here _all_ night?" He says hovering over the two.

Elena's eyes snap open at the sound of Sam's voice. When she realizes she had been sleeping on Dean's chest with his arm wrapped around her, she quickly pushed it off and sat up. Startled by the sudden chaos going around him, Dean was now awoken as well. His eyes squinted as they adjusted to the light. After a few blinks he sees Sam hovering over him with an amused look on his face.

"Sorry to ruin... whatever was going on here," Sam begins.

"Nothing was going on here." Dean replies sternly.

"Yeah, okay. Whatever," Sam disregards Dean's response. "Caroline is looking for you guys." He shoots Elena a look, which she quickly comprehends.

"She's flipping out isn't she?" Elena asks. Sam simply nods. She lets out a sigh before she lifts herself off of the ground. "Alright, I guess I'll go deal with the wrath of Caroline and try to calm her down." She says.

" _Please_ ," Sam pleads. "I'm on grocery duty so..." He turns his attention to Dean who was now lifting himself off of the ground as well. "Dean?"

"Huh?" He gives Sam a perplexed look. "Oh. Groceries? Sounds good."

"Alright, I'll see you guys later then." Elena responds as she smiles and waves them off.

Once Elena is out of hearing distance, Sam turns to Dean with a knowing smile on his face. Dean saw the expression on Sam and was quick to anger.

"Don't you dare say a word, Sam," Dean warned. "I told you nothing happened. We just fell asleep." He explains.

Sam chuckles and raises his hands in defense. "I didn't say anything."

"Yeah, whatever. Let's go to the store." Dean responds, the annoyance in his voice clear. Sam decides to stop bugging Dean about Elena... _For now_.

Elena spent the morning trying to calm down Caroline. Normally she would have conjured up a strategy to calm the blonde's nerves by now, but truth be told; Elena's mind wasn't totally focusing on the words coming out of Caroline's mouth. She'd listen to the rantings of the frantic blonde, but the words wouldn't sink in. They'd go through one ear and come out the other.

Elena's mind was elsewhere; it remained on the beach, the night she spent with Dean. When she woke, she had no time to really process the event of the night before, but now that she's replayed the evening over and over... She felt warmth within her. A warmth that threatened to make her smile whenever she'd replay the night.

Elena was glaring at her reflection in the mirror. The red and white striped dress she was wearing suddenly seemed way too festive for the evening, but she lets out a sigh as she realizes she had no other choice. Caroline had been very vocal about the dress-code for the barbecue; _anyone who lived in the house and was not dressed in the Red, White and Blue colors would be refused and quote Caroline's famous cupcakes"._ Elena knew better than to take that risk. Not only for the cupcakes, but because she knew Caroline would throw a complete fit if she did not abide by the rules.

She reaches into her bag, and searches for the final pieces of her outfit. She pulls out her sleeveless light-blue denim jacket and a pair of white flats. With the final touches added on, she returns to check her image in the mirror once again. She runs her fingers through her long hair. Her normally straight hair had been styled into waves. Feeling satisfied enough with her reflection, she decides she was ready to head down to continue helping Caroline with any last minute preparations.

Just as Elena reaches for the door, the knob twists from the other side. She quickly backs away from the door that was just moments away from colliding with her face. The door opens slightly and Dean pops his head in. He finds Elena standing just a few feet away from the door.

"Sorry, Lena," He apologizes as he finishes making his way into the room. "Didn't know you were th-" he stops mid-sentence.

With his eyes now glued on her, Elena begins to feel self-conscious. Her eyes immediately look down at her dress, wondering if there was some sort of stain she hadn't noticed.

"What is it?" She asks, clearly panicked as she twists and turns trying to find the wardrobe malfunction. "Is there something on my dress?"

Dean shakes his head to recompose himself. "No, Lena," He says, taking a few steps towards her. He gently places his hand on her shoulder to grab her attention. Surprised by his touch, Elena's eyes snap up to meet his. Her heart begins to race having him so close to her.

"Almost forgot how nice you could clean up, Gilbert." He teases; shooting her a wink in the process.

Her racing heart begins to slow down with his response. "Very funny." She shoots back, shrugging out of his grip and quickly begins to make her way past him. The heat in her cheeks was rising, and the last thing she wanted was for Dean to know that he'd just made her blush.

Just before she makes her way out of the door, Dean calls for her. She stops in her tracks, dreading to face him again. She began to pray to any being out there that her cheeks weren't flushed pink when she turned to see him. Mustering up all the courage that she could, she turns to face him, head tilted and arms crossed. She lifted her brows, silently asking him "What?"

Dean chuckles. "I mean it though, Lena. You look nice." He says, reassuringly. Slack-jawed, she's unable to move as what Dean says processes through her mind. "Lena?" He questions, brow furrowed.

Hearing her name called, she shakes off her stunned state. "Yeah," She slightly drops her head to hide the blush that was no doubt beginning to develop in her cheeks. She just barely lifts up her head to meet his gaze. "Uh, Thanks. I guess." She smiles and quickly returns on her path to find Caroline.

-  
The afternoon was clear. The smell of burgers and hotdogs on the grill filled the air as Dean walked out to meet the others. Mary and John had arrived not too long ago. John had already opened up a beer, and was hovering over Sam while they worked the grill. Mary and Elena were helping Caroline set up the food table.

Caroline spots Dean from the corner of her eye. Instantly displeasure overcomes her as she notices Dean was lacking a color in his outfit. Elena spots the situation. Caroline is just about to make her way towards the oblivious man when Elena pulls her back; stopping her from going through with her plan.

"Care! Don't worry. We have those beaded necklaces," She quickly walks over to the box of accessories Mary brought with her. She reaches in and grabs a necklace in each color and raises them up to show Caroline. "See. Now I'll hand these to him, and you should go check on Sam and John. They've probably got a few burgers and hotdogs ready to be taken off the grill." Elena suggests. Caroline lets out a breath and nods.

"Fine," She then looks back at Dean, eyes glaring. This time she makes eye contact with the smiling Winchester, his smile quickly fades as confusion sets in. She scoffs and walks away.

Elena then begins to make her way towards Dean. He raises his hands with wonderment.

"What was that about?" He asks, as Elena reaches him.

Elena lifts the necklaces up. "You forgot Red." She explains. Dean looks down at his clothes, and meets her eyes.

"Really?" He asks surprised by the fact that his outfit was the cause of Caroline's obvious discontent.

"Really." She chuckles, once again lifting the necklaces. Dean lowers his head slightly, allowing for her to slip the trio of necklaces over his head. "There we go," She says as her hands fix the beads from tangling up. "Now she shouldn't have a reason to complain." She smiles at him approvingly.

Dean laughs. "Thanks, Lena."

"Yeah, you better say thanks. I just saved your life." She teases.

Dean rolls his eyes. "I think I could take on Caroline without your help, Gilbert." He laughs.

Elena snorts. "You sure about that?" She lifts her head gesturing towards Caroline. She was now laughing at something Mary had said, but the moment she makes eye contact with Dean her expression turns hard. _If a look could kill…_

Dean then pulls away and looks back at Elena, who was clearly amused by the silent interaction between the two. "Okay fine. I owe you." Dean responds in defeat.

"And I will collect." Elena warns humorously as she begins to walk towards Caroline and Mary.

Although everyone had finished eating their food, they all remained seated at the large picnic table. They enjoyed each other's company, sharing stories, making jokes, everyone bonded effortlessly. Although Elena technically wasn't a part of their family, Mary and John made sure she felt welcomed. They both made sure to ask her questions, curious to find out a little more about the girl Caroline dubbed her "sister from another mister".

"Well, I've still got a couple years until I graduate from medical school and soon after I'll need to spend a couple years as an intern." She responds to John's question about what she was studying.

"What field are you going in?" He asks, clearly impressed by her education.

"I haven't decided, but I'm pretty sure I'll be working with kids. So pediatrics." She explains.

"Impressive." He gives her an approving nod.

"Thank you," She smiles, feeling proud of her work.

"Oh sweetie. When do you ever get time to yourself?" Mary asks sympathetically. "I mean what about a boy. Don't tell me you don't have a cute boy waiting for you at home." Mary leans forward, clearly wanting for Elena to spill the word on her love life.

Elena feels the heat in her cheeks rise up at Mary's question. "Uh," She drops her head, and laughs uncomfortably. Once she lifts her head up, she realizes that everyone at the table had their eyes on her. "I don't," She admits. "I haven't been on a date in a while."

Mary's jaw drops. "But how?"

"Because she says she wants to finish school, before worrying about guys." Caroline says, with a hint of bitterness in her tone.

"Wait, what about Cas?" Sam joins in aswell. Elena's mouth falls open at the realization Caroline had told Sam about Cas. Caroline quickly smacks Sam's arm. "Ow!" He shouts.

"Who's Cas?" Dean asks, interest clearly piqued. Elena meets his eyes for a moment before Mary tries to get her attention back.

"Go on, Elena. I'm interested, who's this 'Cas'?" Mary asks, excitedly.

She once again feels the weight of all eyes on her, she chuckles, bowing her head. "Cas is _just_ my friend," She explains. She then lifts her head back up and focuses her attention on Caroline. "He's the friend I go to when I need to complain about Caroline." Elena says, shooting Caroline a fake smile. The young blonde slumps her shoulders.

Dean then jumps back into the conversation. "What kind of name is Cas for a dude? Sounds nerdy." He chuckles to himself as he takes a swig of his beer.

Mary quickly shoots Dean a look. "Dean." She warns.

He slowly lowers the bottle from his lips. "Sorry, mom." He apologizes.

"Not me, Dean." She gestures towards Elena with her head.

Elena quickly lifts her hand to stop him. "It's not necessary, Mary. Sadly, over the years I've gotten used to your _son's_ childish insults. I've learned to ignore them." She says, locking her gaze with Dean. One side of his lips curls up into half of a smile. He knew she was challenging him, but knew it was only because Mary would be quick to defend. He let her remark slide, and continued with his beer.

Lucky for Elena, John noticed her discomfort and quickly came to her aide by changing the subject not long after the Cas topic came up. They spent about an hour talking about mindless subjects, up until Caroline let out a giant gasp, that startled everyone.

"I'm sorry," She apologizes. "It's almost 8. We should all start moving closer to the beach if we want to get good spots to see the fireworks. Everyone nodded and agreement. They all lifted themselves off of the picnic table, a couple of them groaning from their numb bottoms and stiff legs they've gotten from sitting so long.

"I'm going to go change out of my clothes quickly, you guys can go ahead." Elena says to the group.

"Okay, we'll be on the beach. Look for us there when you're ready!" Caroline exclaims.

Elena nods in response, and turns to make her way back into the house. Once inside, she felt like she could breathe properly. She lets out a giant breath of air she'd been holding in and lets herself relax. Her moment of relaxation doesn't last too long though. The sliding door into the house opens, startling Elena. She quickly turns around with her hand over her heart; only to find Dean standing in the doorway.

"What are you doing here?" She asks.

"There were no more beers in the cooler. I came to check the fridge," He explains, chuckling as he walks past her. He heads for the fridge, and quickly finds a chilled beer. He grabs the bottle, and closes the fridge. He leans against its door, as he effortlessly opens the bottle with his bare hand. He takes a swig of it, and keeps his eyes on Elena.

She felt intimidated by his gaze. "What?" She asks with a hint of anger in her tone.

He shrugs. "I didn't say anything, sweetheart."

"You keep staring." She complains.

"Is it a crime?" He asks mockingly.

She rolls her eyes. "No. But it makes me uncomfortable, so stop it."

An idea sparks up in Dean's mind. A mischievous smile forms on his lips as he begins to take a few steps towards her.

"So you're saying I make you uncomfortable, Lena?" He asks with a tone in his voice, that Elena didn't recognize; but without a doubt caused heart to skip a beat. The closer he got, the more her heart began to race.

Although she was good at keeping her proud posture, Elena was no doubt losing the fight. "Y-yes." She stammers out.

Dean continued to close the space between them, keeping his eyes locked on hers. Once he was close enough, he gently places his hands on her waist. Although Elena stood her ground, his slight touch caused her to completely melt on the inside.

"What are you doing?" She asks.

"Casting my reel." He responds teasingly. She squints her eyes as she looks at him. Normally, she would have pushed him away and responded with something witty by now. But she couldn't. Something inside of her, told her Dean was just as much of a mess as she was.

Without thinking, she wraps her arms around his neck, and pulls him down for a kiss. Initially shock overtakes Dean, but he doesn't fight her off. But just as he's about to deepen the kiss she quickly pulls away, and covers her mouth with her hands.

Eyes wide and red cheeks, she begins to apologize. "Oh my god. I'm so sorry. I didn't mean-"

Dean's hand goes up to his lips feeling the tingling sensation she left. His eyes meet the apologetic brunette's. He knew she wasn't sorry, not _really_. No, she meant it and he enjoyed it.

A silent and tense moment passes, and just as the first firework explodes into the sky, the two simultaneously close the space between them.

Caroline sat between Sam's legs with his arms wrapped around her as they looked up at the fireworks exploding in the sky. Mary leaned against her husband's shoulder, the two enjoying each other's company as the show played out before them. The two couples were so captivated by the spectacle, they had no idea they were missing a certain pair from their group. The two couples had no idea of what was taking place back in the house.

The clothes carelessly came off in almost a blink of an eye. His lips making contact with her bare skin, leaving a trembling trail along the way. Her nails digging into his back, with each jolt of pleasure that he caused. And when they finally reached their peak, the two lay side by side, letting the incident that just occurred between them settle into their minds. The only sounds they heard were their heavy breaths and the cracking fireworks coming from outside.


	6. Sixth

Hearing the footsteps nearing their room, Dean was quick to wake. He managed to slide out from under Elena's resting torso without disturbing her sleep. He scavenged through the piles of clothes that were lying on the ground; trying to find his shirt and his pair of boxers.

As he's slipping his shirt over his head, he hears a knock at the door.

"Elena?" He hears Caroline's voice.

Just as the door knob begins to twist, he takes to giant leaps and appears at the door before Caroline has a chance to poke her head in.

In an attempt to block her view of the room, Dean keeps the door partly closed, as he begins to speak to her.

"Hey, Care. What's up?" He asks.

She crosses her arms and narrows her eyes at him. "I need to see Elena."

"Oh- Well, you see. She's still sleeping…" Dean chuckles and lifts his finger up to his lips; jokingly telling Caroline to lower her voice.  
"I know that," She huffs. "I need to wake her, and tell her we've got to leave earlier than we thought. Sam got a call this morning," She begins to explain. "His college professor got him a meeting with a really good firm, but they want to meet him tonight."

Dean nods in understanding; he takes a moment to decide what to say next. He couldn't let Caroline in the room…

"How about you and Sammy, go on ahead. I don't mind taking Elena home." He offers with a shrug.

Caroline gives him a skeptical look. "Huh…" She breathes out as she looks at the ground; pensive look on her face.

"What?" Dean asks beginning to get concerned.

"You know. I just realized you two have been getting along pretty well this weekend..." She lifts up her head to meet his gaze. "What's going on between you two?" She asks. The words in Dean's throat get caught. He can't think of a single thing to reply.

"You guys are so noisy!" Elena's complaint startles the two of them. Dean turns around and sees her dressed. She gives him a quick wink, and with a sigh a relief he opens the door to let the blonde into the room.

"Oh, Elena. I'm sorry we woke you up," She apologizes as she pushes her way past Dean. "I was just telling Dean that we've got to get going earlier than we planned. Sam got a call from his professor. He's got to be home by tonight for a meeting."  
"Oh," Elena says, slightly disappointed to have to leave so soon. "Okay, I'll get my stuff packed."

Caroline nods her head. "Okay, let us know when you're packed!" She exclaims before exiting the room. Dean shuts the door slowly behind her, and turns to face Elena. The two let out a sigh of relief.

"That was close." Dean grumbles. Elena nods in agreement. A silent moment passes between the two. Neither of them knowing what to say to one another. The memories of the previous night flooding back as they looked at one another. They both knew they needed to speak about what occurred, question was; who would bring it up first?

They both open their mouths to speak, voices over-lapping one another. Dean chuckles awkwardly, and gestures for Elena to start. "You start." He says.

She silently thanks him before letting out what was on her mind.

"What does this mean, Dean?" She asks. "Wha-"

"Sweetheart," He interrupts her. She looks up to meet his gaze and waits for him to speak.

Usually Dean would have said it like it is. _It was fun, but the morning has come and it was time to go our separate ways._ But this time… Looking at her; he couldn't get himself to do it. He wasn't sure what was different. Perhaps it was their history? He couldn't pinpoint the feeling he was getting, all he knew was that he was unable to treat her the way he'd done to many other women before her. She was different, and as much as he hated to admit it, he cared and there was no way he could hurt her.

He runs his hand down his face and lets out an exasperated sigh. She watches him, fear beginning to develop within her as she realizes he was most likely beginning to feel regret. A part of her wished she regretted the night as well. A part of her wished she could accept the lifestyle Dean had grown used to. _We slept together now we move on_. But she wasn't like that. If anything, the previous night had been a wake-up call for her. Those feelings Elena felt for Dean on their first date, those feelings from many years back hadn't never fully gone away. No, they'd just been repressed.

But Elena knew very well she shouldn't expect any more from him.

"Look, Dean," She begins, grabbing Dean's attention. Dean's eyes focused on her, suddenly made her feel vulnerable. Her stomach tightens as she prepares to spout her solution to the problem before them.

"You don't have to worry about giving this," She gestures with her finger between the both of them. "a definition. We slept together, now we move on." She offered with hesitancy in her voice. Her attempt to sound as confident as she could with her solution failed miserably.

"Lena," Dean takes a couple steps towards her. He struggles to find the right words to say to her. "You know I'm not the dating type-" He begins.

"I know," Elena intervenes. "Which is why-"

"Which is why," Dean speaks over her. "I don't think we should try to give whatever this is a definition."

"What are you saying?" She asks, eyes narrowed as she tried to understand where he was heading.

"Why don't you stay?" He asks. Elena tilts her head, silently asking him to elaborate. "I'll drive you back home myself. But in the meantime we can spend a little extra time around here." He offers.

Elena chews on her lip as she considered his offer. The idea of spending some alone time with Dean tempted her too much to reject his offer. "Are you sure?" She asks reluctantly. Dean simply nods in response. "Okaay.." She says as she slowly begins to make her way out of the room. A part of her figured Dean would stop her and take back his offer, but to her surprise; he didn't. She walked right out of the room and made her way down to find Caroline.

Now joined by John and Mary, the group stood outside of the house to say their good-byes.

"Are you sure, Elena?" Caroline asks Elena as they pull away from their embrace. She looks at Elena with stern eyes. "Sam and I can wait for you to pack your things if you changed your mind." She offers.

Elena chuckles and shakes her head. "It'll be fine, Care. Once I return home, who knows when I'll have another chance to take a small vacation like this? I just want to spend a few hours more here, before going back to pulling all-nighters for classes." She pouts.

Caroline nods in understanding. "Fine." She sighs out. She then turns to Dean, arms crossed and a menacing look on her face. "You better behave with Elena, Winchester." She warns him.

Dean points to himself. "Me?" He asks in disbelief. "Why doesn't she get a warning?" He points at Elena.

"Because, dear, we know you." Mary responds jumping into the conversation, as she wraps an arm around Elena. The 3 women now stare down Dean.

Dean opens his mouth to speak, but quickly clamps it back shut. His mother was right; he knew there was no point in arguing with her. Instead he turns to his brother and father for aide. To his surprise, they were staring him down as well.

"We _all_ know you, son." John chuckles.

Dean's jaw drops at his father's response, which causes Sam to burst out laughing. "Alright, alright. Let's give Dean a break," He says as he walks to stand beside Dean.

"Thank you, Sammy. It's nice to know that there's atleast one person -"

"Elena's put up with him for years. She's learned a trick or two to keep him in check. Right?" He asks Elena. She smiles, and nods.

Dean shrugs out of Sam's hold. "What the hell, Sammy!? I thought you were on my side," Dean whines.

Mary pulls away from the group and approaches Dean. "We're kidding, sweetheart." She approaches him and kisses him on his head and pulls him into a hug.

Elena watches the scene playout before her. She looked at Dean in awe, amazed by how he transformed around his family. With his walls down, Dean was a different man. She saw the family man that Dean truly was. She found herself smiling at the thought of it. She knew Dean and Sam were really close, but who would have guessed? Dean was _actually_ a family-man.

Once they say their byes, Elena and Dean watch the two vehicles drive off. Once they were out of visible distance, the two then turn to each other.

"So, now what?" She asks.

"Boardwalk?" He offers.

With a smile on her face, Elena delightfully accepts.

The two spend a few hours on the board-walk; talking to each other just as they did on their first day. The only difference now, was the distance between the two. They walked side by side, hands softly brushing each other as they continued on their path. Eventually, one of them made the first move and took the others hand into their own.

They rode the rides available to them; bumper cars seemed to have brought out the old bickering bone they'd always carried as they would crash into one another on the track. Once they were done with the rides, they continued back onto the boardwalk. As they were walking, they passed by a few game stands. The man managing the booth began to call out to them.

"Hey you, two!" He shouts out at them. Feeling as if they'd been caught, they quickly release their hands from one another. They then turn to face the man who'd been calling them; relief washing over as they realized it was no one of significance. "Come, come play! Pretty bear for pretty lady. Yes?" He lifts his brows up at Dean.

"No," Elena shakes her head. "Thank you." She smiles at the man. She then turns to Dean, but to her surprise he wasn't by her side anymore. She turns back around, and finds him standing at the booth. "Dean, what are you doing?" She asks.

"Come on, Lena. He made a compelling case. Pretty bear for pretty lady." He winks as he pulls out a couple of bills, hands it to the man and receives the game's pistol in return.

"Dean, those games are almost impossible to win," She shakes her head. The man managing the booth shoots Elena an angry scowl, which causes her to giggle and take a few steps towards Dean. He then presses the start button, and the game begins.

Dean raises the shotgun, and focuses on the targets. In less than 30 seconds, he hits 5 targets in a row. The manager and Elena are both taken by surprise by Dean's capability. Once the winner alarm begins to blare, Dean places the gun back onto the booth. The booth manager bitterly hands Dean one of the prizes.

He then turns to Elena, who still had a astonished look on her face.

"What?" He questions her innocently.

"That… That was amazing, Dean!" She exclaims.

"Yeah, well. My uncle Bobby taught me how to hunt as a kid; never could manage to kill anything though. Mostly target practice." He then slightly lifts up the prize. "Clearly my skills have come in handy." He jokes as he hands her the bear.

She takes the bear. "Thank you," She says as heat begins to rise in her cheeks.

"No problem, sweetheart." He responds as he wraps an arm around her. "Pretty bear for a pretty lady." He teases.

"Yeah, yeah." She rolls her eyes dramatically, as they begin to make their way down to the beach.

The sun was beginning to set as the two found a somewhat secluded spot in the sand for them to sit. Once again, side by side; Dean wraps his arm around her again, and she leans her head onto his shoulder. Their eyes glued to the gorgeous sight. The red, orange and yellows; mixing in with the blues and purples of the night sky beginning to approach. The waves lightly crashed onto the shore, just barely reaching their bare feet.

"Dean," She begins to speak. The subject they'd avoided all day had yet to be discussed. As they watched the sun begin to lower, she decided now was the time.

"Yeah?" His eyes remaining on the sunset.

"What happens when we get back?" She asks.

Dean had thought about his answer throughout the day; and to this point he had yet to come up with a single good answer.

"I don't know," He finally responds. "What do you want to happen?" He asks.

Elena now finds herself dumbfounded by Dean's question. She too had thought about an answer throughout the day, but she hadn't mustered up the courage to give her answer. She pulls away from Dean, and readjusts herself so she's facing him. He looks to her, puzzled as he waits for her reply.

"I…" She lets out a breath to calm the nerves turning in her stomach and then begins again. "Dean, we've spent the last few years bickering back and forth. It never once crossed my mind we'd end up here," She chuckles. "But I'm kind of glad we are. I don't know what I want to happen. I haven't been in a relationship in quite some time, and I know you haven't either. I don't want to rush into anything…" Dean sits up, his interest was piqued.

"So?" He asks.

"If you're okay with it… We keep this whole situation between us, and we can continue to see if it turns into something more?" She offers.

Dean considers her offer. It seemed reasonable to him; no real strings attached. It couldn't hurt to try, could it?

"Okay." He responds.

"Okay?" She questions him a small smile beginning to grow on her lips.

"Okay." He repeats smiling as well. She then returns to her spot beside him, and leans her head on his shoulder once again. Their eyes glue themselves back on to what was remaining of the sun. They watch as it slowly makes its way down, leaving them surrounded only by the moonlight.

Once they return home, they carry out Elena's plan. For 8 months, the two are able to keep their " _relationship"_ successfully hidden from their friends and family without rousing suspicion from any loved one. For 8 months, the two connected; opened up to each other and got to know one another on a deeper-lever. On a level neither of them could have ever imagined possible; but yet, neither of the two spoke those 3 words.

Elena knew she had fallen. Without a doubt, she was hopelessly and helplessly in love. And Dean saw this in her eyes when she looked at him. Without her ever having to say a thing, Dean knew exactly what she was feeling and this caused a change between the two. He inadvertently began to distance himself. Their calls were shorter, his visits were less frequent. The walls she managed to knock down were slowly being built up again.

She knew she was beginning to lose him, and it frightened her much more than she cared to admit. Deciding she wasn't willing to let him do this to her, she set up a mandatory date with him. She was determined to lay the cards out on the table; determined to make her feelings known, and what she wanted from him.

Dean wasn't stupid. He knew she was beginning to catch on. He knew she was going to try to fight to make this work. So he didn't show.

She gave him over an hour to show up at their prearranged location. She angrily called his phone, and when it began to lead her straight to voicemail, fury began to boil up. On impulse, she decides to call Caroline.

Once Caroline picks up, Elena lets out a breath to calm her anger.

"Hey, Elena!" Caroline says cheerfully.

"Hey, Care," Elena forces her voice to sound as normal as possible. "I'm sorry to bother you, I was just wondering… have you or Sam seen Dean? I uh… I had a car question."

"Dean? Yeah he and Sam went out to a," She pauses for a moment. "Hold on, Elena." She says. Elena hears shuffling on the other line, before hearing Sam's voice greet Caroline. She pressed the phone against her cheek in an attempt to overhear the conversation. Only thing Elena could make out from Sam was "He ditched me".

"Sorry about that," Caroline apologizes. "Sam went out to a bar with Dean. Guess Dean found a girl and ditched Sam like usual."

 _Dean found a girl_. Those 4 words played in Elena's mind on a loop. She should have known. _"I don't date, sweetheart."_ She should have known.

"Elena are you listening to me?" Caroline's voice brings Elena back from her thoughts.

"Yeah. You said Sam could help. I'll uh… I'll call him if I need him." She replies. Elena hadn't concealed the difference in her tone, and Caroline was quick to catch it.

"Elena, are you okay?" She asks now concerned for her best friend.

"Yeah, I just got to get back to my homework. I'll call you later. Love you!" She exclaims and hangs up the call.

When she got behind the wheel of her car, she didn't know where she was going until she arrived to the location. She parked her car right outside of the apartment building she'd spent so many nights in. She climbed out of her car, and quickly made her way past the front door.

She walked up 3 flights of stairs, deciding that the exercise would help cool down her anger. Once she arrived to his floor, her stomach began to clench. The closer she got to his door, the more frequent her breaths were coming out. Standing in front of his door, with her eyes closed; she musters up the courage to knock. A part of her began to pray that it hadn't been true. A part of her prayed that he would open this door and apologize for standing her up.

Finally, she lifts her hand up to the door, but before she gets to knock; the door opens.

 _She should have known._


	7. Seventh

Just as he thought he day was _finally_ coming to a close, Cas hears a knock at his door. He takes a quick look at his watch; it was just past 1 a.m. He walks over to the door, and checks the peephole. Her head hung, sadly, staring at the ground as she waited for him to open the door. Upon seeing her state, concern fills him. The door swings open, and she lifts her head to meet his gaze.

Cas immediately sees the anguish in her red-rimmed eyes. He tilts his head with a saddened look on his face.

"Hi, Cas…" She chokes out. "Can I…" She drops her head, embarrassed to ask for his help.

The last few months she'd spent with Dean, she'd unintentionally neglected her friendship with Cas. She'd blow him off quite a bit to spend more time with Dean. After a few months, Cas just stopped trying. It wasn't until this night… It wasn't until she had no idea where to go, that she realized just how awful she'd been to him. And she still had the nerve to ask for his help.

Cas gently places his hand on her arm. She lifts her head back up. He doesn't speak a word; he simply nods in response, knowing what she would ask of him. His kindness seemingly hits a nerve, and the tears she'd forced behind a dam, break through and begin to run down her face. He quickly pulls her into an embrace, letting her face fall into his shoulder. He gently caresses her back trying his best to comfort her as her tears begin to dampen his t-shirt.

Elena spent the week with Cas. The condition she'd arrived at his home concerned him greatly so, he insisted she'd stay the entire week and take off those few days of classes. She only agreed because Cas was in the medical field as well. Although he was a few years ahead of her, he could help her catch up if she needed to do so. Not to mention he sweetened his offer by reminding her he was a star student, and he could "easily pull ropes" for her sake.

The week was quiet. Cas wasn't used to seeing Elena down for an extended amount of time. He knew Elena hid most of her pain. He could easily say she was one of the strongest people he'd ever met. He knew her dark past; the losses she's had and the way she always managed to overcome them. So, a part of him knew that she would once again beat this, but he that didn't lessen the anger he felt.

 _How could someone hurt her this way?_ He begins to think to himself. _How could someone be so heartless? She doesn't deserve this._

By the final day, the two sat on his couch, side by side. While Elena stared blankly at the movie playing on the T.V, Cas read through some old emails on his laptop. Without looking over at him, she suddenly speaks up.

"I fell for someone," She says.

Elena's voice startles Cas. He looks over at her, puzzled by her random statement. "What?"

Her eyes now remain on her fidgeting hands as she spoke. "We agreed to keep it between us, because we weren't sure what we were… If we were _anything_ at all," She pauses for a moment. "We didn't want anyone to know, because we didn't want to make a big deal out of it if it didn't work, you know?"

"I understand," Cas responds. His laptop was now shut, and his attention was on her. She lifts her head to meet his gaze. To his surprise, her eyes were glistening. "Elena, you don't have to explain…"

"No," She shakes her head, wiping away a stray tear. "I want to explain to you. I owe you that atleast."

"Okay." He responds.

After another moment, she lets out a sigh and begins again. "I was an idiot,"

"Elena, don't," He begins to say before she cuts him off.

"No, Cas. I really was. I knew what kind of guy he was. I should have known not to get in too deep, but I let myself fall for him. I idiotically believed he felt the same way for me. I idiotically believed he was just scared to let himself fall for me. But worst of all, the moment I realized he was distancing himself, I idiotically believed I could bring him back," She pauses again, to furiously wipe away another set of tears.

"You know," She chuckles. "The night I came here… I decided I was going to finally tell him that I loved him."

"And what happened?"

"He didn't show. And when didn't show, I decided to go over to his apartment,"

"And then?"

Her memories flash back to the woman who opened the door for her. Calling her a "woman" was being generous. The young blonde, looked barely over the legal age.

She drops her head, slightly embarrassed to continue telling her story to Cas. "I just… I should have known, Cas." She responds quietly.

Cas slides over to get closer to her, and wraps his arm around her, pulling her towards his chest. Her head rests on his chest as tears silently begin to stream down her face.

"He didn't deserve you, Elena." He whispers out after a few minutes of silence.

Not knowing how to respond, she just remains in his hold. For the first time in months she feels a small amount of weight lifted off of her chest.

 **March**

The first month was the hardest. When she'd come home from classes, her first instinct had been to pull out her phone and call him. But seeing _his_ name reminded her what'd he done; it reminded her that, that part of her life was over. Going to her bedroom was also a reminder. A reminder of all the nights they'd shared on her bed and her heart ached. Opting to sleep on her couch, it was a long and lonely first month for her.

 **April**

By the second month, she'd broken that habit of wanting to call his phone by calling Cas instead. Rather than spending nights in her own apartment, she found herself over at Cas'. When he wasn't helping her with schoolwork, the two would spend nights watching Netflix and eating take-out until she fell asleep. Although she still had her moments, the second month didn't feel so lengthy and definitely not as lonely.

 **May**

By the third month, Elena still found herself spending time with Cas more often than not. With exams closing in on her, Cas aided Elena with anything she might have needed to make sure she didn't fail these exams. With her mind so preoccupied, she didn't even feel the third month go by.

 **June**

By the fourth month, the two had passed all their courses with flying colors and were finally on their summer break. They both knew they'd earned their time off. They wasted no time in enjoying the beginning of their summer. With the pools finally open for the season again, Elena spent her fourth month laughing at how easily sunburned Cas would get.

 _ **July**_

By the fifth month, Elena hit a block. By the fifth month, Caroline had reached out to her. Caroline informed Elena they were planning another family trip to the beach and Elena had been invited.

"Come on, Elena! I haven't seen you in such a long time. You're always with Cas now." Elena could hear the pout that was no doubt on Caroline's face.

"I know… I'm sorry, it's just… I've been busy with school and Cas helps me a lot." She explains.

"I understand, but come on Elena. You owe me! Come with us, please." She begs. "To sweeten up the deal, I'll have you know, Dean isn't coming this year." And there it was, the ache; hearing his name brought her that ache.

Elena closes her eyes as she fights away that ache. "I… My answer is still no, Care. We can do something when you return okay? I promise." She says. With a sigh, Caroline agrees. The subject then changes and Elena vacantly listens to Caroline on the other end. All she could think about was _him_.

This fifth month was a setback. And Cas could see it in the way she spoke, the happiness that had drained out of her eyes. The wound had somehow opened up again, and he spent that month putting back together whatever pieces may have shattered.

 **August**

By the sixth month, something had changed in Cas. He'd now seen Elena at her worst. He'd now seen how she was able to feint a smile even though she was in agony inside. His view on this woman was changing. He'd always thought she was strong, beautiful, and intelligent. He could spend hours with this woman and he never found himself bored of her. If he was being completely honest, even though they spent almost all their time together, he wanted more. And he spent that sixth month, silently wanting more.

 **September**

By the seventh month, school was back in session; but that didn't stop the two from spending as much time together as they did in the summer. The two spent long nights surrounded by books and sheets. Elena had a tendency of falling asleep first and Cas would soon follow. When Elena would wake, she'd find Cas' sleeping face just a few inches from hers but she wouldn't mind. The seventh month was filled with mornings like this and Elena was perfectly fine with it.

 **October/November**

By the end of the eighth month, another line was crossed. A Halloween party had Cas drinking one drink after another which only led to emotions being expressed as Elena dragged him back home. The next morning Cas awoke with a hangover and horror as the memories flew back into his head. He quickly found Elena in his kitchen whipping up some food.

"Elena," He breathes out. His hand flies up to his aching head.

"Morning," She smiles at him and gestures with the spatula at the table. "Sit. Breakfast is almost ready." She says. He obeys and takes a seat.

Puzzled by her attitude, he began to wonder if it'd just been a dream. Maybe he didn't tell her how he felt. After a few quiet minutes, she walks over to the table with two plates full of food. She sits across from him and they both eat quietly.

The morning flies by and Cas' hangover seems to have been somewhat relieved thanks to Elena's greasy breakfast. She packs her bag, grabs her sweater and begins to head for the door with Cas a few steps behind her. Cas opens the door to let her out.

She takes a step out before turning back to face him. "Oh and Cas?"

"Yes?" He leans against the door.

"I'll be ready for our date by 8. So you can pick me up then." She quickly leans in, wraps her arm around him and places a kiss on his cheek. She then quickly leaves, without giving Cas a chance to say a word.

 **December**

By the eighth month Snow was beginning to fall, which meant the new couple spent a lot of time indoors getting to know a whole other side of each other. Everything about the way he treated her was sweet. He treated her with such care, so much affection. It was different and it took some getting used to, but Elena could adjust.

With Christmas around the corner, they mutually decided they wanted to come out and reveal their relationship to their close family and friends. With assurance that _he_ wouldn't be there, Cas and Elena decided they would take advantage of Caroline's annual Christmas party and come as a couple.

The day came and the two arrived at Sam and Caroline's home, hand in hand. She knocks on the door and gives Cas' hand a squeeze. She could tell he was nervous. Elena had made sure Caroline invited her surrogate father, Alaric and her brother Jeremy. She'd been so excited see him after such a long time, but especially thrilled to introduce him to Cas.

The door opens and reveals the perky blonde. "Merry Christ-" Her eyes go wide as they land on Elena's guest. "Oh my god!" She exclaims loudly.

Hearing Caroline's outburst, Sam quickly makes his way to the front door. "Care, what is it?!" He frantically asks, before looking in the direction her eyes were set on. His eyes then mimic Caroline's expression. "Wow." He breathes out, looking at the smiling couple. Sam gives Caroline a little nudge, bringing her back from the shock.

"I…" She clears her throat. "Wow." She nods. "This was the news, huh?" She asks Elena.

"Yeah, this was it." She says smiling up at Cas.

"Wow… that is… that is just…"

"Great!" Sam quickly intervenes. "It's great. Congrats guys," He says reaching for Elena and giving her a hug. Then gives Cas a quick pat on the back.

"Yeah, it's great." Caroline finally says before also reaching out and giving Elena a long hug. "Oh, this totally means we can double date now!" Caroline exclaims as she releases Elena from their embrace.

"Yeah, Care. That's what it means." Elena chuckles.

Alaric and Jeremy were more than impressed with Elena's new boyfriend. She watched from the opposite side of the living room as the 3 men interacted. She was happy to see them interacting with each other, but for some reason she still felt an ache in her stomach; that same ache that she only felt when she thought of _him_.

And almost as if on cue, she hears his voice from behind her.

"Elena."

Her stomach clenches and her heart begins to race. She slowly turns and faces him for the first time in months.

Just looking into those green eyes again, the ache was gone.


	8. Eighth

If there was one thing Dean was a master at, it was his ability to not care. Or better said _convince_ himself that he didn't care.

The night Elena showed up to his apartment, things didn't exactly go as planned.

 **The night**

 _Feeling that he needed a drink before meeting up with Elena, Dean called his younger sibling to meet up with him at a local bar. The younger Winchester took some convincing, but eventually agreed to meet up with his older brother._

 _By the time Sam showed up at the bar, Dean had already shot down a couple of glasses of something he figured was on the shelf for a few weeks too long, but he didn't mind. He ordered himself another glass, while Sam ordered a beer. Sam watched his older brother shoot down another couple glasses until he decided to intervene._

" _Dean, what the hell is going on?" Sam questions. Dean was a notorious drinker, but Sam knew he wasn't big on the heavy stuff unless something was bothering him, really bothering him._

" _What? Nothing's wrong." Dean replies._

 _Sam scoffs and grabs Dean's glass. He takes a whiff and his face contorts in disgust from the stench. He places the glass back on the counter._

" _Yeah, nothing's wrong." Sam says._

 _Dean considers telling Sam what was going between Elena and him. He knew he could trust his brother, but he also knew what his brother would say. He would tell him what he already knew. Elena was an amazing girl, she was good for him and that he'd be stupid to be questioning his relationship with her. But Dean didn't want to hear that._

 _He already knew these things and that's why he was at a crossroads. He didn't deserve her. He saw the love she had for him and he knew she deserved more. Someone who could provide her with the future she would want. Elena was in school, studying to become a pediatrician. Dean worked an 8 to 7 job fixing up busted vehicles. His money went to fast food, alcohol and he still struggled month to month with his rent._

 _He knew Elena well enough to know that these things didn't bother her. She wasn't that type of girl. She cared for him no matter what. But that didn't change the way Dean saw her. He knew in the future she secretly would want more from him. Stuff he wouldn't be able to provide. She deserved more._

" _Dean?" Sam's voice works to break Dean's train of thought. Dean turns to his brother. "What?" He mutters._

" _Are you gonna tell me what's going on?"_

 _Dean takes a sip from the beer Sam had ordered for him. "Yeah…" He pauses for another moment, to consider once again if he should tell his brother what'd been going on or not. Ultimately he decides not to. "Just the normal, rent, job's killing me… I just needed to go out and do something fun."_

 _Sam looks at his brother incredulously, not fully believing his story. "You sure?" Sam insists._

" _Yes, Sam. Jeez, is it wrong of me to want to hang out and drink a little with my brother?"_

 _Sam sighs. He could tell Dean was keeping something from him, but he wouldn't be able to get any information out from him tonight; so he drops it. "Fine."_

 _The two spend about an hour chatting about when Dean's eyes begin to roam around the bar. With the alcohol running through his stream, Dean began to feel like his normal self again. He wasn't thinking about Elena anymore. His mind was simply focused on the present._

 _He'd been eying a girl for quite a bit of the time that he'd been there. Reaching the point to where one of them just needed to give the signal. The young blonde takes her lip between her teeth and gives Dean the look. And with that he takes another swig of his beer and plops it down on the counter._

" _Looks like I've got an invitation to attend to, little brother." Dean pats Sam's back. "Catch up with you later?" He says as he shrugs on his coat._

 _Sam scoffs. He should have figured Dean would do this to him, always ditching. Sam finishes his last sip of beer and soon after is leaving the bar as well._

 _Slamming him against his apartment door, Dean struggled to peel himself away from her as he tried to unlock the door. The girl Dean had picked up had no intentions on wasting any time._

" _Hold on, sweetheart." He says between the kisses. "Gotta open the door." She lets out a sigh and releases him._

 _Letting out a breath of relief, he inserts his key into the keyhole and opens the door. She walks in, eying the place, noting the simplicity of it all. An old couch, a t.v, empty beer cans scattered in various places. The record player caught her attention._

" _Wow, I've never seen one of these in real life. These things are like ancient." She says._

" _Yeah," He chuckles. "Was sort of a hand-me-down from my father."_

 _She rolls her eyes. "Ugh, I wouldn't have taken it. It's big and bulky. Takes up a lot of room." She says eying the place once again._

 _Dean bites his tongue, fighting back the urge to tell her to go screw herself. He didn't want to ruin this night with her. He didn't know why, but he had the need to just have this night._

" _Yeah," He fakes a laugh. He then grabs her by her waist and spins her around to face him. "Now, where were we?" He asks with a smug smile._

" _I believe we were here…" She says before leaning forward and letting her lips land on his. The two once again, begin what they'd started just a half an hour prior. Tongues exploring one another, hands roaming around their bodies, the two were caught in the heat, the lust._

 _Her hands slowly began to make their way under his shirt. Her long nails, gently scratching against his stomach and that's when he pulls away. Those weren't_ _ **her**_ _nails,_ _ **her**_ _hands._

" _What's wrong, baby?" She purrs in his ear._

" _Uh…" Dean shakes his head. "Nothing, just…let's move this, shall we?" He asks, gesturing towards his bedroom._

 _She nods and begins to pull him towards the room. Upon reaching the foot of the bed, she quickly shoves him onto the mattress and climbs on top. Once again, she wastes no time in leaning down and beginning with her kisses restarting what they'd begun._

 _Her hands frantically begin to unbutton his shirt and once she's successful; her hands land on his bare chest. Nails, for the second time; scratch against his skin._ _ **She**_ _gradually begins to come into his mind again. As much as he tried to fight it off, it was hopeless._

" _I can't," He says, slightly pushing the girl off of him._

" _You can't what, baby?" She asks before leaning down and putting her lips on his chest._

 _Dean lets out a sigh and again attempts to push her off. She remains straddled on him and looks down at him curiously._

" _Why not? I thought we were having a good time… I thought you wanted this…"_

 _Dean shakes his head again. "It's…"_

 _The girl rolls her eyes. "Ugh, don't you dare use the 'it's not you, it's me line." She says as she climbs off of him. Dean sits up on the bed as she angrily begins to put on her shorts. "Of course I went after one that's whipped." She begins to mutter to herself._

 _Whipped?_

" _Sweetheart, I ain't whipped." Dean chuckles._

" _Oh please," She sneers. "I could see it in the way you were drinking. But I figured hey, he's hot. And maybe just maybe it was a work issue, rather than love life. But boy was I wrong."_

 _She begins to walk out of his room and he quickly follows behind her._

" _I'm not whipped!" He insists._

" _Look," She stops just in front of the door. "I don't really care. You have no reason to explain to me your love life or your apparent lack of one. But when you're ready to have fun, don't hesitate to call. My offer still remains." She winks at him and turns back to open the door, only to find Elena with her hand mid-air._

 _Immediately Dean feels a pit in his stomach._

" _Oh," The girl says. "Hi." She smiles, stretching her hand out to Elena._

 _Elena's eyes flicker between the girl's smile and the shocked looked on Dean's face._

 _After a few beats of Elena not responding to the girl's gesture, she drops her hand._

" _Alright then… He," She points at Dean. "and I are done… so… I guess I'll get going." She says and quickly makes for her escape._

 _Now alone, the two stand there in silence. Elena's eyes trained on Dean's unbuttoned shit and disheveled hair. Upon realizing the image she was getting, Dean quickly attempts to cover up._

" _Lena…" He begins to speak._

 _She raises her hand to quiet him. "It's fine." She says without looking into his eyes._

" _But, Elena…" He attempts again, only to be cut off again._

" _I said its fine." She repeats. "We never said we were exclusive…" This time Dean keeps his mouth shut. He knew nothing he said beyond this point mattered anymore. The look on Elena's face said it all. He'd destroyed her. And this was much easier for him. She could finally see what kind of man he was._

" _I'm going to go…" She says, finally meeting his eyes. He saw the tears were already beginning to well up in her eyes and as much as it hurt him to see her like this, he kept a straight face._

" _Okay." He says._

 _She closes her eyes for a brief moment and takes in a breath of air. "Okay." She breathes out and turns to make her way out of the building. And although the tears had already formed, she forced herself to keep them in. Keep them in until she reached her car._

 _As soon as those doors closed…_

 _Dean fell against his door_

 _Elena gripped tight on her wheel_

 _And the dams broke._

 **Present**

"What are you doing here?" She asks him. A part of her felt this moment was surreal. As if he was just an illusion.

"I actually, came to see you." He admits.

"Why?"

"Because we need to talk."

"About what, Dean?" She pushes, slightly irritated.

"You know what, Lena."

"I can't. I'm here with someone." She hastily turns away from him, but Dean grabs her by her arm before she gets a chance to take a step.

"5 minutes and then I'll let you got back to Casper over there."

She rolls her eyes. " _Tiel_. Cas- _TIEL_ ," She corrects him.

"Yeah, whatever. You know what I mean."

She lets out an exasperated sigh. "Fine."

His grip remains on her arm as he pushes through the crowd of people, leading her to the empty dining room. He closes the glass door behind him, making sure they'd have their privacy.

"Okay, what?" She questions once the door was shut.

He turns to face her. He tried preparing for this moment. He'd come up with different speeches, scenarios, but all of that preparation went down the drain. He was frozen, dumbfounded. _How to begin?_

Mustering up any courage that he could, he decides to start from the beginning. "Lena… that night…" He begins, but is quickly cut off before he gets a chance to go further.

She lets out a sigh and crosses her arms. "I told you I didn't need an explanation, Dean."

"Will you just hear me out?" He asks. She clamps her mouth shut and nods. "Nothing happened between me and that girl,"

She scoffs. "You really expect me-"

" _Hear me out_." He repeats.

Again she closes her mouth and lets him continue.

"Yes, I'd brought her back with the intentions of _something_ to happen," He admits, the guilt building up within him. "but nothing did. I couldn't…" He trails off.

"Why not?" She asks her interest clearly piqued.

"Because of you."

 _Because of her?_ He couldn't possibly mean… No. _No._

"And that, you expect me to believe that?"

"Yes, Elena. Because it's true. Nothing happened."

She takes a moment. The sincerity in his eyes told her one story, but her memory of the night told her another.

"Fine," She begins. "Let's say I do believe this story. Why didn't you tell me before? Why did you wait until _now_ to tell me this?"

He shrugs. "It was easier for me…"

"What does that even mean?" She questions.

He pinches the bridge of his nose. "I'm not like that guy you have out there, Elena." He sighs. She gives him a puzzled look, so he begins again. "I fix cars for a living, barely making the monthly rent. I couldn't tell you which bone is connected to which bone. I'm not like _him_."

"And you think that matters to me, Dean?" Her irritation rose slightly from his assumption of her.

"No. That's exactly why it was easier for me to end things, the way that I did…"

"I'm not following."

He throws his head back in frustration. _Why is this so difficult?_ He thinks to himself.

He takes a moment to piece his thoughts together, finding a better way to get to where he needed to get.

He locks his eyes with hers, and begins again. "I was afraid."

Her brows furrow as she tilts her head curiously. "Of what?"

"Of you, the future," He takes a few steps towards her. "I was afraid that I wasn't good enough for you. That eventually you'd see that…" He drops his head in shame.

Having him so close, her heart began to race. She tries to find her voice. "What changed your mind?" She finally says.

He lifts his head back up to meet her eyes. "I… I'm not sure but," He takes her hand in his. "I can't deny that I miss you, Lena."

Her eyes flicker back and forth between his. Those feelings she thought had gone away rush through the surface washing over her and bringing her back to where she was almost a year's time. He was so close she could simply lean in and kiss him…

"No," She shakes her head and takes her hand out of his. She turns her back on him. "You can't do that," She then turns to face him again with fire in her eyes. "You can't do what you did, disappear for months and expect me to be okay with it; for it to be all forgiven."

"I'm not asking for that, Elena."

"Then what do you want from me?" She asks, crossing her arms again.

"A chance." He says calmly.

"You had one." She spits back quickly.

"Yeah," He nods his head. "I had my chance and I know I screwed it up," He takes a few paces towards her, closing the distance between them. He lifts his hand up to her face, cupping her cheek in the palm of his hand. "I know now how stupid I was, baby," His touch on her skin, the pet name; they sent shivers down her spine.

She raises her hand and places it on top of his. She was letting herself melt around him, around his charm. The magnetic pull they used to share was stronger than ever and she wanted so much to give in.

But she couldn't. "No," His heart twinges as she pulls away from his touch again. "No, Dean. I've moved on. I'm with Cas."

"Yeah, I noticed that, Elena." He says bitterly.

"I… I'm sorry." She whispers out before turning towards the door.

"Wait," He calls out as she reaches for the handle.

She pauses and by the time she looks up to face him, Dean had already closed the space between them and was now only a few feet away. He quickly takes her face in his hands and leans down to crash his lips onto hers. As much as she wanted to fight it, she couldn't. The shock the kiss sent through her body caused her heart to race. The longer their lips remained lock, the deeper she fell into it. So was no longer fighting those feelings, she'd lost the battle. She couldn't deny it; she'd never stopped loving him.

When they've both become breathless, they finally pull apart. Dean leans his forehead against hers; the pants coming from the two of them are the only sound in the room for a good minute.

"Do you still love me?" He asks, keeping his forehead against hers, eyes closed.

But before Elena gets to reply, a soft knock at the door causes the two to open their eyes. They quickly look in the direction of the door, only to find Sam and Cas standing at the glass door.


	9. Ninth

**Last December**

 _She dragged her feet up the last flight of stairs before reaching her floor. She let out a sigh of relief once she reached the top. She continues to walk towards her apartment, mindlessly searching through her keys for her home key. Once she reaches her door, a slight panic begins to settle in as she realizes her door wasn't completely closed._

 _She digs out her phone from her pocket and hesitates before pushing the door open. Clutching on her phone for dear life, she takes a step into the dark apartment. Her first instinct is to flip the switch to turn the lights on, but when she flips the switch, nothing happens._

" _Elena?" She hears a man's voice._

 _Immediately she grabs her phone and begins to dial 9-1-1._

" _I'm calling the cops!" She warns._

" _Wait no! Baby, it's me." He says grunting as he collides with an end table._

" _Dean?" She questions, squinting in the darkness to get a better view._

" _You got someone else callin' you baby?" He responds, his voice getting closer to her._

 _She flips her phones flashlight on and aims it directly at him. Being only a few feet away from her, the brightness of the light caused him to squint._

" _What are you doing here? And why isn't my electricity working?" She asks._

 _He shoves his hands in his pockets and stares at the ground as he begins to speak. "I… kind of hijacked your extra pair of keys."_

" _Okay, but why?"_

" _Well…" He steps closer to her. "I sort of had a surprise for you."_

 _He takes the phone from her hand, and then grabs her hand with his free one. With the small light he's able to navigate the both of them safely through the darkness to the further end of her apartment. Upon reaching it, he hands her phone back._

" _Take a look for yourself." He says proudly._

 _Taking the phone from him, she then aims the light directly in front of her. To her surprise, she finds a green object right before her. Upon closer inspection, she then realizes it was a Christmas tree. She moves the light from top to bottom, as she views the different ornaments he'd decorated the tree with._

" _You did this all on your own?" She questions._

 _Dean's hand flies to the back of his neck. "Yeah," He admits. "I think I connected the lights wrong or something. When I plugged it into that socket, the electricity in the whole apartment blew out." He chuckles._

 _She lets out a soft giggle. "It's nothing with your lights. That outlet doesn't work right. That's why I never bothered putting anything electrical in that corner."_

" _Oh… I'm sorry."_

" _No, no. Dean, don't be," She turns to him now. "This is absolutely amazing, and… Thank you." She says, as she snakes her arms around his neck and pulls him down for a kiss._

" _Mmm, I should do more surprises if I get thanked like this." He says against her lips._

" _And that's not all of it," She teases between kisses. She then turns the flash light off, as the two sink deeper into their embrace._

 **Present**

"Well, this is awkward." Dean says, breaking Elena's train of thought.

She slightly pushes him away from her, and takes a few steps towards Cas and Sam.

"Cas…" She begins. Cas drops his head and lets out a soft laugh, without looking at her he turns away and begins to walk. "Cas, wait!" She begins to go after him, but is stopped by Dean's grip around her wrist. She turns to face Dean, puzzled.

"Elena, we weren't done…"

"Let her go, Dean." Sam interjects, his tone angered. Dean meets his brother's eyes and the two exchange a silent conversation until finally Dean releases her from his grasp.

Dean feels a pang of hurt as he watches her run after Cas. Once she's out of viewing distance, he meets his brother's gaze once again.

"What the hell was that all about?" Sam asks. "I thought you said you were just going to talk to her, Dean."

Dean shrugs. "Look, man. She obviously still has feelings for me. She wouldn't have let me kiss her…"

"That doesn't matter, Dean! Clearly, she was trying to move on and you probably just destroyed that for her," Sam watches as Dean's shoulders slump. Guilt washes over him seeing his brother in this condition. He closes his eyes as he pinches the bridge of his nose.

"Dean," Sam sighs out. "Look, I get it. You regret doing what you did to her, and I get you want to make things right. But you have to realize… You may have waited too long. I'm not exactly sure how long this thing with her and Cas has been going on, but I doubt it's something completely new."

"What are you saying?"

"I'm saying, you may need to let her go."

"Cas, please talk to me." She pleads. The whole car ride back to her apartment, Cas had been silent. She waited for him to blow up, to scream, to do anything but nothing. He drove in silence, his eyes focused only on the road.

"Please," She pleads again. "Say something, anything. Scream, shout. _Anything_."

Once the car is parked, he turns off the vehicle and lets his head fall back onto the headrest. He let all his emotions, his thoughts process in his mind, but he couldn't focus on one single emotion to aim at her. He knew he wanted to be angry, because he knew seeing her… kissing _him_ ; the guy who was without a doubt the one who had broken her. The reason why, Cas spent the last 8 months fixing her, healing her wounds. So, seeing her with him… well that hurt.

It hurt him and anger was the first emotion he felt, but he couldn't focus on that one.

He hadn't said it to her yet, because they'd just only started their relationship; but Cas knew he had loved Elena for quite some time. Even before all of this happened, his world always seemed light up just a little more by seeing her laugh. He always had admired her from a distance, but keeping her as a close friend, afraid to pursue for more. But something changed, he finally had the girl, and he wasn't going to give her up without a fight.

After a few minutes of silence to let his thoughts process, he finally turns to face her. His eyes flicker back and forth, searching in her guilt ridden ones. Once again, he drops his head slightly.

"You know, Elena… I have always admired you," He begins. "You have never failed to surprise me. You seemingly have the entire package wrapped up within you. Your kindness, your intelligence, your strength," He pauses and meets her gaze. " _Your beauty_." He breathes out.

"Cas, I'm so sorry…" She begins before he cuts her off again.

"I know you are… and it is one of the many reasons of why I love you," He pauses to watch her reaction as he let the words slip out.

Her eyes slightly widen at the revelation. "You love me?" She asks.

He chuckles and shakes his head. "Are you really that surprised by that?" He lifts his brows at her. She blushes slightly before he continues. "I know you would not do anything to purposefully harm me, because I know over the years; specifically within the last few months… our friendship has grown into this more profound bond. And I know you love me too, Elena. But not in the way that I want you to." He sighs.

Again, she stays silent. She had nothing to respond, because what he was saying was true, but she didn't want to further harm him.

"I already knew you still had feelings for him. I just thought maybe with time, you could learn to have feelings for me too, that eventually the feelings for me would over power the ones for him. And I still stand by that, Elena. Knowing what I know, I still believe you are able to fall for me, if you just give me a chance… a _real_ chance."

"What do you mean?" She asks.

"I was going to bring this up on New Year's, but… I think now is a better time than ever," He forces a smile. "I got early acceptance in the internship program at a hospital in Seattle."

"What?" Her eyes widen at the news. "Cas, oh my god that's so great!" She leans in and pulls him into a hug.

Once she settles back into her seat, he keeps the forced smile on his face. "Yeah," He nods.

"Why don't you seem excited about it as I am?" She asks. He tilts his head, and she then quickly realizes the answer. "Oh," She breathes out. "You'd have to move there…"

He nods. "I have until the end of January to give my response because the program starts up in mid-February… And Elena… I want you to come with me."

Her eyes widen. "What?"

"I know it is a big step. Moving across country, leaving the comfort of your home, friends and family behind… But this could be a new start, a start for the both of us. They have a great school where you can finish off your studies…"

"Cas," She begins but Cas is quick to cut her off.

"I'm going to accept the spot, because this is important to me, Elena. I'm not forcing you to answer tonight. Take a few days, a week, or the entire month if you need to. But I want you to think about it, _really_ think about it."

"Okay." She nods.

"Alright then." He smiles before leaning in and quickly pressing his lips against hers. Once he pulls away, she gives him one last wave before climbing out of the vehicle.

She watches as he starts the car and keeps her eyes on the vehicle as it begins to drive off.

"Well, that took long enough." A deep familiar voice says from behind her.

Immediately she turns around as her hand flies up to her heart.

"What the hell? Dean!" She shouts angrily.

"Sorry, sweetheart. Didn't mean to scare ya." He smirks.

She rolls her eyes. "What are you even doing here?"

"You left without answering my very important question." He teases.

She scoffs, and pushes past him to make her way into her building. Dean quickly sneaks his way behind her as she steps in.

"Dean, seriously. Go home." She says with an annoyed tone as she begins to climb the stairs.

Dean ignores her remark and follows behind her only to suddenly bump into her when she suddenly stops in the middle of the stairs. She snaps her head back to look at him, eyes glaring. He rolls his eyes as he pushes past her, and finishes climbing the flight. Once he reaches the landing, his eyes turn back to find Elena with her arms crossed and feet firmly planted on that middle step.

"Elena, come on. Don't be like that." He pleads.

"Go home, Dean." She repeats.

"Not until you answer my previous question." He retorts.

"Fine," She quickly begins to climb up the stairs. "I don't. Okay? There. Now go home." She says as she reaches the landing and attempts to rush past him. Unfortunately he's quick and has a hold of her arm before she gets to the next set of stairs.

"No, I don't buy that." He says as he pulls her to face him.

"Well," She pauses for a minute. "You should, because it's true. I told you, I'm with Cas."

He chuckles. "Yeah, I'm aware. But tell me, sweetheart," He releases her arm, and places his hand on her back, as he pulls her closer to him. "Does he make your heart race like I do when I'm close to you?" He questions.

She swallows thickly.

He then lifts his free hand up to her cheek, gently caressing the soft skin with his thumb, leaving a trail of a tingling sensation until he reaches her lips. "Does he know how you like to be kissed?" He leans in slightly, bringing his own lips to hers; keeping them just a few centimeters from each other. And just like that, she was putty all over again. She wraps her arms around his neck, and uses the tips of her toes to lift herself and close the small space between their lips.

She lets herself melt around him, as they stumble back into her apartment. The problems that may lie outside of the safety of her bed mattered no more. All that mattered was that the emptiness that she wasn't aware existed within her, was now filled. With each touch, each pull, each grunt, each moan, each kiss, and the familiarity of it all. She didn't know how much she needed him, how much she craved him until he was back.

And when the two finished, with her head resting on his bare chest and his arm wraps securely around her, she's finally able to say those words.

"I still love you." She whispers out, as she listens to the deep snores emitting from chest.

A tear escapes and runs down her before she finally closes her eyes, and lets unconsciousness take over.


End file.
